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

HRID 1610180Notes

Reaction equation

HRID 1610180 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 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1,1-dimethylethyl (1RS,2RS)-2-(4-fluorophenyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethylcarbamate (2.1 g, 5.08 mmol) in ethanol (25 ml) was added 20% hydrogen chloride ethanol solution (25 ml) and the mixture was heated under reflux for 1 hr. The reaction solution was evaporated under reduced pressure, and the residue was washed with diethyl ether to give (1RS,2RS)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine hydrochloride (1.7 g, 96%).

Workup

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

Sources & evidence

ORD record
ord-e303a34fec144a129ee60fabe8f8508c
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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