[vanillin.eugenol.demethylation.methylation]  [2-heac.nitroaldol.condensation]  [nabh4.copper.reduction]  [zn.hcl.reduction]  [back]

 Reduction of Organic Compounds with Sodium Borohydride-Copper(II) Sulfate System, S. Yoo et al., Korea Research Institute of Chemical Technology, 16.05.1990
 Transition metal catalyzed NaBH4 MeOH reduction, A. Rahman et al., Department of Chemical Engineering, King Saud Universit, 01.09.2011
 P2NP to amine with NaBH4-Copper. One pot, no messing with metals or acids, testex, The Vespiary - Drug Synthesis & Extraction, 15.04.2017  [1] [2] [3] [4] [5] [6]  [pdf]
 Nitrostyrene reduction using NaBH4/CuCl2, karlar, Sciencemadness Discussion Board, 11.07.2018  [pdf]

 1  2
 1. Adding CuSO4 to rxn mixture, aes256, The Vespiary - Drug Synthesis & Extraction, 05.11.2021
 2. Crystal clear Amphetamine floating on top after steam distillation, chaddywhyskers, reddit - r/TheeHive, 01.08.2020

general procedure:
add nabh4 (7.7 mol eq.) to ipa and water and stir until everything dissolved. then add the nitroalkene (1 mol eq.) in small portions (allow to react until the yellow colour has disappeared before adding the new portion). dissolve cucl2 (0.1 mol eq.) in water and add to the reaction mixture in one portion. reflux for one hour (one drop every two seconds). steam distill (if amine is steam volatile) or normal a/b workup.


2-(2,5-dimethoxyphenyl)ethanamine,
 name  [2c-h] [swgdrug]  molweight  cas number  melting point
1,4-dimethoxy-2-[(E)-2-nitroethenyl]benzene (substrat) 209.20 40276-11-7
2-(2,5-dimethoxyphenyl)ethanamine freebase (product) 181.23   3600-86-0
Hydrochlorid acid   36.46
2-(2,5-dimethoxyphenyl)ethanamine hydrochloride (product) 217.69   3166-74-3 139

2-(3,4,5-trimethoxyphenyl)ethanamine
 name  [m]  molweight  cas number  melting point
1,2,3-trimethoxy-5-[(E)-2-nitroethenyl]benzene (substrat) 239.22 6316-70-7
2-(3,4,5-trimethoxyphenyl)ethanamine freebase (product) 211.26
Sulphuric acid   98.08
2-(3,4,5-trimethoxyphenyl)ethanamine sulphate (product) 309.34 5967-42-0 183 186

1-(4-Fluorophenyl)propan-2-amine
 name  [4-fa]  molweight  cas number  melting point
1-fluoro-4-[(Z)-2-nitroprop-1-enyl]benzene (substrat) 181.16 437717-48-1
1-(4-Fluorophenyl)propan-2-amine freebase (product) 153.20
Hydrochlorid acid   36.46
1-(4-Fluorophenyl)propan-2-amine hydrochloride (product)   189.70 64609-06-9 152 154

1-(2,4,5-Trimethoxyphenyl)propan-2-amine
 name  [tma-2]  molweight  cas number  melting point
1,2,4-trimethoxy-5-(2-nitroprop-1-enyl)benzene (substrat) 253.25 17231-84-4
1-(2,4,5-Trimethoxyphenyl)propan-2-amine freebase (product) 225.29
Hydrochlorid acid   36.46
1-(2,4,5-Trimethoxyphenyl)propan-2-amine hydrochloride (product)   261.74 15995-72-9 188 189

1-(1,3-benzodioxol-5-yl)propan-2-amine
 name  [mda]  molweight  cas number  melting point
5-(2-Nitroprop-1-enyl)-1,3-benzodioxole (substrat) 207.18 5438-41-5
1-(1,3-benzodioxol-5-yl)propan-2-amine freebase (product) 179.22
Hydrochlorid acid   36.46
1-(1,3-benzodioxol-5-yl)propan-2-amine hydrochloride (product)   215.67 6292-91-7 187 188