Hydrochloric Acid → (1R,2S)-2-(Trifluoromethyl)cyclohexanamine hydrochloride

HRID 1696221Notes

Reaction equation

HRID 1696221 reaction equation
C1([C@H]([NH:9][C@@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]2[C:16]([F:19])([F:18])[F:17])C)C=CC=CC=1.[ClH:20]>C(O)C.[OH-].[OH-].[Pd+2]>[ClH:20].[F:17][C:16]([F:18])([F:19])[C@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][C@H:10]1[NH2:9]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67278095(1R,2S)-N-[(1R)-1-phenylethyl]-2-(trifluoromethyl)cyclohexanamine

Product 1

HCID 67277264(1R,2S)-2-(Trifluoromethyl)cyclohexanamine hydrochloride

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (1R,2S)—N-[(1R)-1-phenylethyl]-2-(trifluoromethyl)cyclohexanamine (3.53 g) and 13 mL of HCl (2M ethanol solution) in 35 mL of ethanol was added Pd(OH)2(2.78 g) under N2. H2 gas was purged and stirred for 2 days under 4 atm at 60° C. Pd(OH)2 was filtered off through a pad of Celite. Solvent was removed under reduced pressure. (1R,2S)-2-(Trifluoromethyl)cyclohexanamine hydrochloride (2.37 g) was obtained as a white solid.

Workup

  1. customH2 gas was purged
  2. filtrationPd(OH)2 was filtered off through a pad of Celite
  3. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d549203afc32441a9038154cf4a853e8
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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