Production Method 1

1637648-95-3

953789-37-2

Reaction Conditions

1.1 Reagents: Chlorotrimethylsilane ,  Aluminum chloride ,  Sodium borohydride Solvents: Tetrahydrofuran ;  rt → 70 °C; 24 h, 70 °C; 70 °C → rt
1.2 Reagents: Water
1.3 Reagents: Sodium hydroxide Solvents: Water ;  30 min, pH 14, rt
1.4 Reagents: Hydrochloric acid Solvents: Ethyl acetate ;  30 min, rt

Reference

A Concise Synthesis of Racemic Lorcaserin

Xu, Bin; Su, Jincai; Wang, Jing; Zhou, Guo-Chun, Australian Journal of Chemistry, 2016, 69(7), 770-774

Production Method 2

2486273-06-5

953789-37-2

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Water ;  rt → 120 °C; 2 h, 120 °C

Reference

Preparation method of lorcaserin

, China, , ,

Production Method 3

847063-13-2

953789-37-2

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Toluene ,  Dimethylacetamide ;  50 - 55 °C; 20 - 30 min, 50 - 55 °C; 55 - 60 °C; 3 - 4 h, 55 - 60 °C; 25 - 30 °C
1.2 Solvents: Isopropanol ;  30 min, 25 - 30 °C

Reference

Process for preparation of lorcaserin intermediate

, China, , ,

Production Method 4

78-96-6

32327-70-1

953789-37-2

Reaction Conditions

1.1 1 h, 80 °C → 93 °C; 2 h, 90 - 95 °C
1.2 Solvents: Chlorobenzene ,  Water ;  95 °C → 74 °C; 15 min, 70 - 75 °C; 75 °C → 50 °C
1.3 Reagents: Thionyl chloride ;  55 min, 56 °C → 64 °C; 4 h, 60 - 65 °C
1.4 Solvents: Isopropanol ;  65 °C → 67 °C; 67 °C → reflux; 2 h, reflux

Reference

Processes for preparation of 2-chloro-N-(4-chlorophenethyl)propan-1-amine hydrochloride

, World Intellectual Property Organization, , ,

Production Method 5

78-96-6

6529-53-9

953789-37-2

Reaction Conditions

1.1 rt → 90 °C; 45 min, < 100 °C; 90 min, 85 - 100 °C; 100 °C → 50 °C
1.2 Solvents: Water
1.3 Reagents: Thionyl chloride Solvents: Isopropanol ;  0 - 5 °C; 2 min, 0 - 5 °C; 1.5 - 2.5 h

Reference

Processes for preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine and intermediates

, World Intellectual Property Organization, , ,

Production Method 6

847063-13-2

953789-37-2

Reaction Conditions

1.1 Reagents: Thionyl chloride Catalysts: Dimethylformamide Solvents: Toluene ;  1 h, 45 - 65 °C; 1 h, 55 - 60 °C; 2 h, 0 - 5 °C

Reference

Process for preparation of Lorcaserin hydrochloride hemihydrate

, China, , ,

Production Method 7

1638542-85-4

953789-37-2

1431697-94-7

Reaction Conditions

1.1 Catalysts: Aluminum chloride ;  rt → 85 °C
1.2 Reagents: Sodium chloride Solvents: Water ;  20 °C
1.3 Solvents: Dichloromethane ;  overnight, 20 °C
1.4 Reagents: Sodium hydroxide Solvents: Water

Reference

Development and optimization of a new synthetic process for lorcaserin

Cluzeau, Jerome; Stavber, Gaj, Bioorganic & Medicinal Chemistry, 2018, 26(4), 977-983

Production Method 8

1463880-66-1

953789-37-2

Reaction Conditions

1.1 Reagents: Boron trifluoride etherate ,  Sodium borohydride Solvents: Tetrahydrofuran ;  30 min, 0 - 5 °C
1.2 Solvents: Tetrahydrofuran ;  0 - 5 °C; 4 - 5 h, 60 - 65 °C; 65 °C → 20 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  15 min, 10 - 20 °C
1.4 Reagents: Hydrochloric acid Solvents: Toluene ,  Water ;  30 min, 30 - 40 °C
1.5 Reagents: Sodium hydroxide Solvents: Water ;  pH 11 - 13
1.6 Reagents: Hydrochloric acid Solvents: Water ;  15 - 30 min, pH 2 - 4, 0 - 20 °C

Reference

A process for the preparation of lorcaserin hydrochloride

, India, , ,

Production Method 9

953789-37-2

Reaction Conditions

Reference

Processes for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates related thereto

, United States, , ,

Production Method 10

847063-13-2

953789-37-2

Reaction Conditions

1.1 Reagents: Thionyl chloride Catalysts: Dimethylacetamide Solvents: Toluene ;  5 - 10 min, 50 - 60 °C; 3 h, 60 - 65 °C

Reference

A process for preparing 1-[[2-(4-chlorophenyl)ethyl]amino]-2-propanol and its salts

, China, , ,

Production Method 11

1030624-41-9

953789-37-2

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Toluene ,  Dimethylacetamide ;  rt → 50 °C; 50 - 60 °C; 2.5 h, 60 °C → 65 °C

Reference

Processes for preparing (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine intermediates toward serotonin-2C (5-HT2C) receptor agonists

, World Intellectual Property Organization, , ,

Production Method 12

847063-13-2

953789-37-2

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Toluene ,  Dimethylacetamide ;  rt; < 60 °C; 27 min, < 60 °C

Reference

Microwave-assisted synthesis of lorcaserin hydrochloride

Zeng, Bi-tao; Zhu, Tao; Wang, Tian-xia, Huaxue Shiji, 2016, 38(9), 917-920

Production Method 13

34164-14-2

953789-37-2

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  1 - 2 h, 0 - 10 °C
1.2 Reagents: Boron trifluoride etherate ;  0 - 10 °C; 2 h, 60 - 65 °C
1.3 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ;  5 - 15 °C; 1 h, 90 - 100 °C
1.4 Reagents: Sodium hydroxide Solvents: Water ;  15 min, pH 8.5 - 9.5, 5 - 15 °C
1.5 Reagents: Hydrochloric acid Solvents: Water ;  2 h, pH 1 - 2, 5 - 15 °C

Reference

An improved process for the preparation of lorcaserin hydrochloride intermediate n-(4-chlorophenethyl)-2-chloropropan-1-amine or salt thereof

, India, , ,

Production Method 14

78-96-6

1875-88-3

953789-37-2

Reaction Conditions

1.1 Reagents: Phosphorus tribromide ;  3 h, 80 °C; 80 °C → rt
1.2 Reagents: Water ;  rt
1.3 4 h, 90 °C; 90 °C → rt
1.4 Reagents: Thionyl chloride Catalysts: Dimethylacetamide Solvents: Toluene ;  3 h, 70 °C
1.5 Reagents: Water

Reference

Process for preparing a chlorophenylethylpropanamine compound

Anonymous, IP.com Journal, 2015, 16, 1-3

Production Method 15

847063-13-2

953789-37-2

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Dimethylformamide ,  Toluene ;  3 h, 65 °C

Reference

Synthesis of Lorcaserin and method for preparing intermediate of Lorcaserin

, China, , ,

Production Method 16

78-96-6

1875-88-3

953789-37-2

Reaction Conditions

1.1 Reagents: Hydrogen bromide ;  rt → 100 °C; 4.5 h, 1.38 - 1.93 bar
1.2 85 °C; 2 h, 85 - 95 °C
1.3 Reagents: Thionyl chloride Solvents: Toluene ,  Dimethylacetamide ;  50 °C; < 60 °C; 4 h, 60 - 65 °C

Reference

Processes for preparation of 4-chloro-N-(2-chloropropyl)-benzeneethanamine hydrochloride

, World Intellectual Property Organization, , ,

Production Method 17

953789-37-2

Reaction Conditions

Reference

Processes for preparing (r)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates thereof

, United States, , ,

Production Method 18

953789-37-2

Reaction Conditions

Reference

Process for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

, China, , ,

4-Chloro-N-(2-chloropropyl)benzeneethanamine Hydrochloride Raw materials

• 1-Aminopropan-2-ol
• 4-Chloro-N-(2-chloro-1-oxopropyl)benzeneacetamide
• 2-(4-chlorophenyl)ethan-1-ol
• 2-(4-Chlorophenyl)ethyl Chloride
• 1-((4-Chlorophenethyl)amino)propan-2-ol Hydrochloride
• N-[2-(4-Chlorophenyl)ethyl]-N-(2-chloropropyl)-4-methylbenzenesulfonamide
• 1-(2-Bromoethyl)-4-chlorobenzene
• 1-((4-Chlorophenethyl)amino)propan-2-ol
• Propanamide,2-chloro-N-[2-(4-chlorophenyl)ethyl]-
• Benzeneethanamine, 4-?chloro-?N-?2-?propen-?1-?yl-?, hydrochloride (1:1)
• 4-Chloro-N-(2-chloropropyl)benzeneacetamide

4-Chloro-N-(2-chloropropyl)benzeneethanamine Hydrochloride Preparation Products

• (Rac)-Lorcaserin hydrochloride (1431697-94-7)
• 4-Chloro-N-(2-chloropropyl)benzeneethanamine Hydrochloride (953789-37-2)

• 1. Fe3O4 nanoparticle chains with N-doped carbon coating: magnetotactic bacteria assisted synthesis and high-rate lithium storage?
  Dan Yang,Yanping Zhou,Xianhong Rui,Jixin Zhu,Ziyang Lu,Eileen Fong,Qingyu Yan RSC Adv., 2013,3, 14960-14962
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  Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. Llewellyn Chem. Commun., 2007, 3291-3293
• 5. Establishment and implications of a characterization method for magnetic nanoparticle using cell tracking velocimetry and magnetic susceptibility modified solutions
  Huading Zhang,Lee R. Moore,Maciej Zborowski,P. Stephen Williams,Shlomo Margel,Jeffrey J. Chalmers Analyst, 2005,130, 514-527

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Phenethylamines

4-Chloro-N-(2-chloropropyl)benzeneethanamine Hydrochloride: A Comprehensive Overview

4-Chloro-N-(2-chloropropyl)benzeneethanamine Hydrochloride (CAS No. 953789-37-2) is a versatile organic compound with significant applications in various fields of chemistry and materials science. This compound, often referred to as 4-chloro-N-(2-chloropropyl)benzeneethanamine hydrochloride, is characterized by its unique chemical structure, which includes a benzene ring substituted with a chlorine atom and an ethanamine group linked to a 2-chloropropyl chain. The hydrochloride salt form of this compound enhances its stability and solubility, making it suitable for a wide range of industrial and research applications.

Recent advancements in synthetic chemistry have led to the development of novel methods for the synthesis of 4-chloro-N-(2-chloropropyl)benzeneethanamine hydrochloride. Researchers have explored various reaction pathways, including nucleophilic substitution and condensation reactions, to optimize the synthesis process. These methods not only improve the yield but also ensure the purity of the final product, which is crucial for its application in sensitive areas such as pharmaceuticals and electronics.

The structural properties of 4-chloro-N-(2-chloropropyl)benzeneethanamine hydrochloride make it an ideal candidate for use in drug design and development. Its ability to form stable complexes with metal ions has been extensively studied, particularly in the context of creating new generations of catalysts for organic transformations. For instance, recent studies have demonstrated its potential as a ligand in transition metal-catalyzed reactions, significantly enhancing reaction efficiency and selectivity.

In addition to its role in catalysis, 4-chloro-N-(2-chloropropyl)benzeneethanamine hydrochloride has found applications in polymer chemistry. Its ability to act as a cross-linking agent has been leveraged in the development of advanced materials with tailored mechanical and thermal properties. For example, researchers have utilized this compound to synthesize high-performance polymers for use in aerospace and automotive industries, where durability and resistance to extreme conditions are paramount.

The electronic properties of 4-chloro-N-(2-chloropropyl)benzeneethanamine hydrochloride have also been explored in the context of organic electronics. Its conjugated system allows for efficient charge transport, making it a promising candidate for use in organic light-emitting diodes (OLEDs) and photovoltaic devices. Recent studies have highlighted its potential as a hole transport material in OLEDs, contributing to improved device performance and longevity.

From an environmental perspective, the synthesis and application of 4-chloro-N-(2-chloropropyl)benzeneethanamine hydrochloride have been scrutinized to ensure sustainability. Researchers have developed eco-friendly synthesis routes that minimize the use of hazardous solvents and reduce waste generation. Furthermore, efforts are underway to explore its biodegradability and assess its impact on ecosystems, ensuring that its use aligns with global sustainability goals.

In conclusion, 4-Chloro-N-(2-chloropropyl)benzeneethanamine Hydrochloride (CAS No. 953789-37-2) is a multifaceted compound with immense potential across diverse scientific disciplines. Its unique chemical properties, coupled with recent advancements in synthesis and application techniques, position it as a key player in driving innovation in materials science, pharmaceuticals, and electronics. As research continues to uncover new possibilities for this compound, its role in shaping future technologies is expected to grow significantly.

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