Production Method 1

58095-77-5

15596-07-3

94-62-2

Reaction Conditions

1.1 Solvents: Tetrahydrofuran

Reference

Three-component synthesis of (E)-α,β-unsaturated amides of the piperine family

Schobert, Rainer; Siegfried, Sven; Gordon, Gary J., Journal of the Chemical Society, 2001, (19), 2393-2397

Production Method 2

1802004-79-0

94-62-2

Reaction Conditions

Reference

A metal-free approach for transamidation of amides with amines in aqueous media

Srinivas, Mahesuni; Hudwekar, Abhinandan D.; Venkateswarlu, Vunnam; Reddy, G. Lakshma; Kumar, K. A. Aravinda; et al, Tetrahedron Letters, 2015, 56(33), 4775-4779

Production Method 3

736947-76-5

94-62-2

Reaction Conditions

1.1 Reagents: Potassium hydroxide ,  Alumina Solvents: Dichloromethane ,  Dibromodifluoromethane

Reference

Stereoselective synthesis of piperamide alkaloids by modified Ramberg-Baecklund reaction

Li, Yang; Zhang, Yu; Wang, Xiao Long; Huang, Zhi; Cao, Xiao Ping, Chinese Chemical Letters, 2004, 15(6), 631-634

Production Method 4

736947-76-5

94-62-2

Reaction Conditions

1.1 Reagents: Potassium hydroxide ,  Alumina Solvents: Dichloromethane ,  Dibromodifluoromethane ;  1 h, rt

Reference

Stereoselective synthesis of naturally occurring unsaturated amide alkaloids by a modified Ramberg-Baecklund reaction

Li, Yang; Zhang, Yu; Huang, Zhi; Cao, Xiaoping; Gao, Kun, Canadian Journal of Chemistry, 2004, 82(5), 622-630

Production Method 5

50838-22-7

94-62-2

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Dimethyl sulfoxide ,  Water ;  30 min, rt
1.2 6 - 8 h, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

Identification and optimization of piperine analogues as neuroprotective agents for the treatment of Parkinson's disease via the activation of Nrf2/keap1 pathway

Wang, Lun; Cai, Xiaoying; Shi, Mingsong; Xue, Linlin; Kuang, Shuang; et al, European Journal of Medicinal Chemistry, 2020, 199,

Production Method 6

136-72-1

94-62-2

Reaction Conditions

1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine

Reference

Addition of carbon nucleophiles to aldehyde tosylhydrazones of aromatic and heteroaromatic-compounds: total synthesis of piperine and its analogs

Chandrasekhar, S.; Reddy, M. Venkat; Reddy, K. Srinivasa; Ramarao, C., Tetrahedron Letters, 2000, 41(15), 2667-2670

Production Method 7

57134-53-9

158504-70-2

94-62-2

Reaction Conditions

1.1 Reagents: Catecholborane
1.2 Reagents: Sodium carbonate Catalysts: Potassium hydroxide ,  Palladium diacetate Solvents: Ethanol

Reference

New access to conjugated dien- and enamides. Synthesis of dehydropipernonaline, pipernonaline and related biologically active amides

Kaga, Harumi; Ahmed, Zaheer; Gotoh, Kohei; Orito, Kazuhiko, Synlett, 1994, (8), 607-8

Production Method 8

38489-76-8

10043-37-5

94-62-2

Reaction Conditions

1.1 Reagents: Triethylamine ,  N-Bromosuccinimide ,  Lithium chloride Catalysts: Triphenylantimony ,  Palladium diacetate ,  1-Butanaminium, N,N,N-tributyl-, 2,2,2-trifluoroacetate (1:1) Solvents: Dichloroethane

Reference

Catalytic Hunsdiecker reaction and one-pot catalytic Hunsdiecker-Heck strategy: synthesis of α,β-unsaturated aromatic halides, α-(dihalomethyl)benzenemethanols, 5-aryl-2,4-pentadienoic acids, dienoates and dienamides

Naskar, Dinabandhu; Roy, Sujit, Tetrahedron, 2000, 56(10), 1369-1377

Production Method 9

203378-07-8

94-62-2

Reaction Conditions

1.1 Reagents: Trifluoromethanesulfonic anhydride ,  2-Iodopyridine Solvents: Dichloromethane ;  15 min, -20 °C
1.2 Reagents: Triethylamine ,  Benzeneseleninic acid ,  Dess-Martin periodinane Solvents: Dichloromethane ;  2 h, rt; 5 min, -20 °C; 5 - 60 min, -20 °C → 25 °C
1.3 Reagents: Sodium carbonate Solvents: Water ;  25 °C

Reference

Chemoselective α,β-Dehydrogenation of Saturated Amides

Teskey, Christopher J.; Adler, Pauline; Goncalves, Carlos R.; Maulide, Nuno, Angewandte Chemie, 2019, 58(2), 447-451

Production Method 10

136-72-1

94-62-2

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Dichloromethane

Reference

A Short, Efficient, and Stereoselective Synthesis of Piperine and its Analogues

Bauer, Adriano; Nam, Jun-Hyun; Maulide, Nuno, Synlett, 2019, 30(4), 413-416

Production Method 11

58095-77-5

1796-25-4

94-62-2

Reaction Conditions

1.1 Reagents: Benzenemethanamine, 4-ethenyl-N,N-diethyl-, polymer with 1,1′-[1,4-butanediylbis… Solvents: 1-Propanol ;  24 h, 80 °C

Reference

Chromatography-Free Wittig Reactions using a Bifunctional Polymeric Reagent

Leung, Peter Shu-Wai; Teng, Yan; Toy, Patrick H., Organic Letters, 2010, 12(21), 4996-4999

Production Method 12

136-72-1

94-62-2

Reaction Conditions

1.1 Reagents: Diisopropylethylamine ,  1-[Bis(dimethylamino)methylene]-1H-benzotriazolium hexafluorophosphate(1-) 3-oxi… Solvents: Dimethylformamide ;  8 h, rt

Reference

The development of novel cytochrome P450 2J2 (CYP2J2) inhibitor and the underlying interaction between inhibitor and CYP2J2

Tian, Xiangge; Zhou, Meirong; Ning, Jing; Deng, Xiaopeng; Feng, Lei; et al, Journal of Enzyme Inhibition and Medicinal Chemistry, 2021, 36(1), 737-748

Production Method 13

136-72-1

94-62-2

Reaction Conditions

1.1 Reagents: Sodium methoxide Solvents: Methanol ;  20 h, reflux

Reference

Method for synthesis of piperine

, China, , ,

Production Method 14

136-72-1

94-62-2

Reaction Conditions

1.1 Reagents: 2,4-Dichloro-6-methoxy-1,3,5-triazine Catalysts: Dabco Solvents: Ethyl acetate ;  30 min, rt
1.2 Reagents: Diisopropylethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Ethyl acetate ;  30 min, rt; 1 h, rt

Reference

Catalytic and Sustainable Amide Bond Formation using a DABCO/Dichlorotriazine System

Adler, Pauline ; Gras, Marion ; Smietana, Michael, ChemCatChem, 2023, 15(10),

Production Method 15

136-72-1

94-62-2

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Dichloromethane ;  10 min, cooled; rt; 2 h, rt
1.2 Solvents: Dichloromethane ;  2 - 2.5 h, 60 °C

Reference

Synthesis, Antimicrobial, Antioxidant and Nematicidal Activity of (2E,4E)-5-(Benzo[d] [1,3]dioxol-5-yl)penta-2,4-dienamides

Wahab, Aneela; Sultana, Amina; Khan, Khalid Mohammed; Sherwani, Sikandar K.; Perveen, Zeba; et al, Journal of the Chemical Society of Pakistan, 2015, 37(5), 1008-1014

Production Method 16

136-72-1

94-62-2

Reaction Conditions

1.1 Reagents: 1,1-Dimethylethyl 1-(1,1-dimethylethoxy)-2(1H)-isoquinolinecarboxylate Solvents: Dichloromethane ;  30 min, rt
1.2 24 h, rt

Reference

Carboxamidation of carboxylic acids with 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI) without bases

Saito, Yukako; Ouchi, Hidekazu; Takahata, Hiroki, Tetrahedron, 2008, 64(49), 11129-11135

Production Method 17

136-72-1

94-62-2

Reaction Conditions

1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  rt; 18 h, rt

Reference

Method for synthesizing piperine from 5-(1,2-methylenedioxyphenyl)-2-pentenal by oxidation and condensation

, China, , ,

Production Method 18

136-72-1

94-62-2

Reaction Conditions

1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  rt

Reference

Synthesis of (E,E)-Dienones and (E,E)-Dienals via Palladium-Catalyzed γ,δ-Dehydrogenation of Enones and Enals

Pan, Gao-Fei; Zhang, Xing-Long; Zhu, Xue-Qing; Guo, Rui-Li; Wang, Yong-Qiang, iScience, 2019, 20, 229-236

Production Method 19

203378-07-8

94-62-2

Reaction Conditions

1.1 Reagents: Pivalic acid Catalysts: Cupric acetate ,  Palladium diacetate ,  1,1′-[1,2-Ethanediylbis(sulfinyl)]bis[benzene] Solvents: Acetonitrile ;  24 h, 100 °C

Reference

Synthesis of conjugated dienes via palladium-catalyzed aerobic dehydrogenation of unsaturated acids and amides

Keerthana, Meledath Sudhakaran; Jeganmohan, Masilamani, Chemical Communications (Cambridge, 2022, 58(63), 8814-8817

Production Method 20

675-20-7

136-72-1

94-62-2

Reaction Conditions

1.1 Reagents: Oxalyl chloride Solvents: Dichloromethane ;  0 °C; 0 °C → rt; 4 h, rt
1.2 Solvents: Toluene ;  rt; rt → reflux; 16 h, reflux

Reference

Environmentally Benign Transamidation Protocol for Weakly Nucleophilic Aromatic Amines with N-Acyl-2-piperidinones: Catalyst-, Additive-, Base- and Solvent-Free Condition

Rajan, Ida Angel Priya Samuel; Subramani, Muthuraman; Pushparathinam, Gopinath; Rajendran, Saravanakumar, Asian Journal of Organic Chemistry, 2022, 11(9),

Piperine Raw materials

• 3,4-(Methylenedioxy)cinnamic acid, pred.trans
• 4-Penten-1-one, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-, (4E)-
• (E)-3,4-Methylenedioxycinnamaldehyde
• 5-Ethynylbenzod1,3dioxole
• (2E,4E)-5-(1,3-Benzodioxol-5-yl)-2,4-pentadienamide
• 1-(piperidin-1-yl)prop-2-en-1-one
• (Triphenylphosphoranylidene)ketene
• piperidin-2-one
• 1-(1-Oxobut-2-enyl)piperidine
• (E,E)-Piperic Acid
• 1-(Bromoacetyl)piperidine
• Piperidine, 1-(3-bromo-1-oxo-2-propenyl)-, (E)-
• Piperidine, 1-[[[(2E)-3-(1,3-benzodioxol-5-yl)-2-propenyl]sulfonyl]acetyl]-

Piperine Preparation Products

• Piperine (94-62-2)

• 1. Evolution of shape, size, and areal density of a single plane of Si nanocrystals embedded in SiO2 matrix studied by atom probe tomography
  Bin Han,Yasuo Shimizu,Gabriele Seguini,Celia Castro,Gérard Ben Assayag,Koji Inoue,Yasuyoshi Nagai,Sylvie Schamm-Chardon,Michele Perego RSC Adv., 2016,6, 3617-3622
• 2. Emergence of microfluidic wearable technologies
  Joo Chuan Yeo,Kenry Lab Chip, 2016,16, 4082-4090
• 3. Fast-pulsing NMR techniques for the detection of weak interactions: successful natural abundance probe of hydrogen bonds in peptides?
  Amandine Altmayer-Henzien,Valérie Declerck,David J. Aitken,Ewen Lescop,Denis Merlet,Jonathan Farjon Org. Biomol. Chem., 2013,11, 7611-7615
• 4. 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
• 5. Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials?
  Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-Garayoa RSC Adv., 2017,7, 24133-24139

• Solvents and Organic Chemicals Organic Compounds Alkaloids and derivatives Alkaloids and derivatives
• Solvents and Organic Chemicals Organic Compounds Alkaloids and derivatives

• 2373-80-0(3,4-Methylenedioxycinnamic acid)
• 591-95-7(1,2-Pentadiene)
• 23887-46-9(Cinepazide)
• 10354-27-5(1-(3,4-Methylenedioxyphenyl)-1-penten-3-one)
• 23434-88-0(Tetrahydropiperine)
• 7780-20-3(5-(1,3-dioxaindan-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one)
• 25775-90-0((Z)-Capsaicin)
• 26472-00-4(Methylcyclopentadiene dimer)
• 19408-84-5(Dihydrocapsaicin)
• 2444-46-4(Nonivamide)