Production Method 1

94749-73-2

97664-55-6

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Potassium iodide Solvents: Dimethyl sulfoxide ;  25 °C
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Process for the preparation of salmeterol xinafoate from 2-(bromoethyl)benzene

, China, , ,

Production Method 2

629-03-8

3360-41-6

97664-55-6

Reaction Conditions

1.1 Reagents: Potassium hydroxide Catalysts: Tetrabutylammonium bromide Solvents: Toluene ;  10 h, rt
1.2 Reagents: Triethylamine Catalysts: Potassium iodide Solvents: Acetonitrile ;  30 min, 45 °C; 45 °C
1.3 Reagents: Oxalic acid Solvents: Methanol
1.4 Reagents: Sodium hydroxide Solvents: Water ;  pH 7

Reference

An Efficient and Practical Synthesis of Salmeterol

Lu, Yongping; Xu, Xinliang; Zhang, Xingxian, Organic Preparations and Procedures International, 2015, 47(2), 168-172

Production Method 3

13633-25-5

629-11-8

97664-55-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Toluene ;  3 - 4 h, 40 - 50 °C; 5 h, 100 - 110 °C
1.2 Reagents: Triethylamine ;  15 °C → 10 °C
1.3 Reagents: Methanesulfonyl chloride ;  4 h, 0 - 10 °C; 4 h, 0 - 10 °C
1.4 Reagents: Sodium hydroxide Solvents: Water ;  < 35 °C
1.5 < 35 °C; 10 h, 100 - 110 °C

Reference

Preparation of salmeterol and salts thereof

, India, , ,

Production Method 4

97664-55-6

Reaction Conditions

Reference

Phenethanolamine derivatives

, Belgium, , ,

Production Method 5

135235-81-3

97664-55-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Toluene ;  12 h, rt → 110 °C

Reference

Preparation of the salmeterol intermediate fumarate crystal

, China, , ,

Production Method 6

94749-73-2

97664-55-6

Reaction Conditions

1.1 Reagents: Triethylamine ,  Sodium iodide ;  30 min, 45 °C
1.2 -

Reference

A convenient synthesis of (R)-salmeterol via Rh-catalyzed asymmetric transfer hydrogenation

Liu, Juntao; Zhou, Di; Jia, Xian; Huang, Ling; Li, Xingshu; et al, Tetrahedron: Asymmetry, 2008, 19(15), 1824-1828

Production Method 7

94749-73-2

97664-55-6

Reaction Conditions

1.1 Reagents: Triethylamine ,  Sodium iodide Solvents: Dimethyl sulfoxide

Reference

A new synthetic approach to salmeterol

Rong, Yajing; Ruoho, Amold E., Synthetic Communications, 1999, 29(12), 2155-2162

Production Method 8

629-11-8

3360-41-6

97664-55-6

Reaction Conditions

1.1 Reagents: Triethylamine ,  Methanesulfonyl chloride Solvents: tert-Butyl methyl ether ;  0 - 10 °C; 10 °C → rt
1.2 Reagents: Diisopropylethylamine Solvents: Toluene ;  40 h, reflux
1.3 Reagents: Triethylamine Solvents: tert-Butyl methyl ether ;  rt → 0 °C
1.4 Reagents: Methanesulfonyl chloride ;  0 - 10 °C; 10 °C → rt
1.5 Reagents: Triethylamine Solvents: Acetonitrile ;  7 h, reflux
1.6 Reagents: Oxalic acid Solvents: Methanol ;  reflux; cooled; 1 h, 15 - 25 °C
1.7 Reagents: Sodium hydroxide Solvents: Ethyl acetate ,  Water ;  basified, rt

Reference

Process for the synthesis of N-substituted [6-(4-phenylbutoxy)hexyl]amine synthons useful in the synthesis toward Salmeterol xinafoate

, Spain, , ,

Production Method 9

94749-73-2

97664-55-6

Reaction Conditions

1.1 Reagents: Cesium carbonate Solvents: Dimethylformamide ;  5 h, 60 - 80 °C

Reference

Improved synthesis of 13C, 2H3- and 2H3-salmeterol by Cs2CO3-mediated monoalkylation of a primary amine

Molinski, Tadeusz F.; Stanley, Scott D., Journal of Labelled Compounds & Radiopharmaceuticals, 2002, 45(9), 755-762

Production Method 10

135235-81-3

97664-55-6

Reaction Conditions

1.1 Solvents: Acetonitrile ;  overnight, rt

Reference

A new route for synthesis of salmeterol xinafoate

Wu, Xiaochun, Xinan Shifan Daxue Xuebao, 2009, 34(4), 85-88

Production Method 11

97664-55-6

Reaction Conditions

Reference

New process and intermediates for the preparation of α1-[6-(4-phenylbutoxy)hexylaminomethyl]-4-hydroxy-1,3-benzenedimethanol [salmeterol].

, Spain, , ,

Production Method 12

97664-55-6

Reaction Conditions

Reference

Enantioselective synthesis of salmeterol via asymmetric borane reduction

Hett, Robert; Stare, Ragnar; Helquist, Paul, Tetrahedron Letters, 1994, 35(50), 9375-8

6-(4-Phenylbutoxy)hexylbenzylamine Raw materials

• 1-Bromo-4-phenylbutane
• Benzene,[4-[(6-bromohexyl)oxy]butyl]-
• 1-Hexanol, 6-(4-phenylbutoxy)-, 1-methanesulfonate
• 1,6-Hexanediol
• 1,6-Dibromohexane
• 4-Phenyl-1-butanol

6-(4-Phenylbutoxy)hexylbenzylamine Preparation Products

• 6-(4-Phenylbutoxy)hexylbenzylamine (97664-55-6)

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Introduction to Compound with CAS No. 97664-55-6 and Product Name: 6-(4-Phenylbutoxy)hexylbenzylamine

The compound with the CAS number 97664-55-6 and the product name 6-(4-Phenylbutoxy)hexylbenzylamine represents a significant advancement in the field of chemical biology and pharmaceutical research. This compound, characterized by its unique structural framework, has garnered attention for its potential applications in drug development and therapeutic interventions. The molecular structure of 6-(4-Phenylbutoxy)hexylbenzylamine consists of a benzylamine core substituted with a hexyl chain and a 4-phenylbutoxy group, which contributes to its distinct pharmacological properties.

Recent studies have highlighted the compound's role in modulating various biological pathways, making it a promising candidate for further investigation. The presence of the 4-phenylbutoxy moiety is particularly noteworthy, as it has been shown to influence the compound's solubility and bioavailability, key factors in drug formulation. Additionally, the hexylbenzylamine component suggests potential interactions with neurological receptors, which could be exploited for therapeutic benefits.

In the realm of medicinal chemistry, the synthesis and characterization of 6-(4-Phenylbutoxy)hexylbenzylamine have opened new avenues for research. Advanced computational methods, such as molecular dynamics simulations and quantum mechanical calculations, have been employed to elucidate its interactions with biological targets. These studies have revealed that the compound exhibits high affinity for certain enzymes and receptors, suggesting its utility in developing novel therapeutic agents.

One of the most exciting aspects of this compound is its potential in addressing neurological disorders. Preliminary research indicates that 6-(4-Phenylbutoxy)hexylbenzylamine may interact with serotonin and dopamine receptors, which are implicated in conditions such as depression and Parkinson's disease. The benzylamine moiety, in particular, has been identified as a key pharmacophore responsible for these interactions. Further investigation is warranted to fully understand its mechanism of action and therapeutic potential.

The structural features of 6-(4-Phenylbutoxy)hexylbenzylamine also make it an attractive scaffold for drug design. By modifying specific functional groups, researchers can fine-tune its pharmacological properties to target specific diseases or conditions. For instance, altering the length of the hexyl chain or substituting the 4-phenylbutoxy group with other bioactive moieties could lead to compounds with enhanced efficacy or reduced side effects.

Moreover, the compound's solubility profile has been a focus of recent research. The combination of hydrophilic and lipophilic groups in its structure allows it to dissolve in both aqueous and organic solvents, facilitating its use in diverse formulations. This property is particularly important for developing oral medications or topical treatments where bioavailability is a critical factor.

Industrial applications of 6-(4-Phenylbutoxy)hexylbenzylamine are also being explored. Its unique chemical properties make it suitable for use as an intermediate in synthesizing more complex molecules. Additionally, its stability under various conditions makes it a reliable component in pharmaceutical formulations requiring long shelf lives.

Future research directions include exploring the compound's interactions with other biological targets and evaluating its potential in preclinical studies. Collaborative efforts between academic institutions and pharmaceutical companies are essential to accelerate these investigations. The insights gained from these studies could pave the way for new treatments targeting neurological disorders and other diseases.

In conclusion, 6-(4-Phenylbutoxy)hexylbenzylamine, with its CAS number 97664-55-6, represents a significant advancement in chemical biology and pharmaceutical research. Its unique structural features and potential applications make it a promising candidate for further investigation. As research continues to uncover new insights into its pharmacological properties, this compound holds great promise for improving human health and well-being.

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