Ethanol hydrochloride → (1RS,2RS)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine hydrochloride

HRID 1610189Notes

Reaction equation

HRID 1610189 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:29])[CH:9]([NH:21]C(=O)OC(C)(C)C)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.C(O)C.[ClH:33]>C(O)C>[ClH:33].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:29])[CH:9]([NH2:21])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 865932161,1-dimethylethyl (1RS,2RS)-2-(4-fluorophenyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethylcarbamate

Product 1

HCID 22261728(1RS,2RS)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine hydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1,1-dimethylethyl (1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethylcarbamate (2.58 g, 6.24 mmol) in ethanol (35 ml) was. added 20% hydrogen chloride ethanol solution (35 ml) and the mixture was heated under reflux for 30 min. The reaction solution was evaporated under reduced pressure and the residue was washed with diethyl ether. to give (1RS,2SR)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine hydrochloride (2.05 g, 94%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 min
  3. customThe reaction solution was evaporated under reduced pressure
  4. washthe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-e982130529804bc8b3160b79de912bed
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…