Hydrochloric Acid → 2-(3,4-Dichlorophenyl)propan-1-amine hydrochloride

HRID 2265176Notes

Reaction equation

HRID 2265176 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:12])[C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8].B.C1COCC1.CCO.Cl>C1COCC1.CCOCC.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:12])[CH2:10][NH2:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 2723981Borane;tetrahydrofuranHCID 687696262-(3,4-Dichlorophenyl)propanenitrile

Product 1

HCID 687713402-(3,4-Dichlorophenyl)propan-1-amine hydrochloride

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(3,4-Dichloro-phenyl)-propionitrile (5.0 g, 25.0 mmol) was dissolved in THF (80 mL). BH3.THF (1 M in THF, 27.5 mL, 27.5 mmol) was added and the mixture was stirred overnight at rt. EtOH (10 mL) was added, the mixture was stirred for 20 min, and HCl in Et2O (2 M, 12.5 mL) was added. After stirring for 1 h, water was added, causing precipitation of the product. The product was collected by suction filtration and dried (4.2 g, 70%). MS (ESI+): mass calcd. for C9H11Cl2N, 204.1; m/z found, 205 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.45-7.42 (m, 2H), 7.17-7.15 (m, 1H), 3.05-3.02 (m, 2H), 2.98-2.96 (m, 1H), 1.24 (d, J=6.5, 3H).

Workup

  1. stirringthe mixture was stirred for 20 min
  2. stirringAfter stirring for 1 h
  3. customprecipitation of the product
  4. filtrationThe product was collected by suction filtration
  5. customdried (4.2 g, 70%)

Sources & evidence

ORD record
ord-e92e3d0a8e8b4b8f98a8fa7e12173ebd
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

Loading…