Benzylamine → HCID 178520974, compound

HRID 1530819Notes

Reaction equation

HRID 1530819 reaction equation
[H][H].[OH:3][CH:4]([CH:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1)[C:5]([F:8])([F:7])[F:6].[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CO.[Pt]>[CH2:16]([NH:23][C@H:12]1[CH2:13][CH2:14][C@@H:9]([CH:4]([OH:3])[C:5]([F:8])([F:7])[F:6])[CH2:10][CH2:11]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 212527094-(1-Hydroxy-2,2,2-trifluoroethyl)cyclohexanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 178520974HCID 178520974, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

At 50° C. and a hydrogen pressure of 5 bar, 43.0 g of 4-(1-hydroxy-2,2,2-trifluoroethyl)cyclohexanone and 24.0 g of benzylamine in 400 ml of methanol were hydrogenated in the presence of 1.5 g of platinum (5% on carbon). The catalyst was filtered off and the mixture was concentrated. The cis/trans isomers were separated by silica gel chromatography (ethyl acetate/ethanol 9:1). The cis isomer eluted first of the two isomers, to give the title product as a colourless oil.

Workup

  1. customAt 50° C.
  2. filtrationThe catalyst was filtered off
  3. concentrationthe mixture was concentrated
  4. customThe cis/trans isomers were separated by silica gel chromatography (ethyl acetate/ethanol 9:1)
  5. washThe cis isomer eluted first of the two isomers

Sources & evidence

ORD record
ord-edf21f0f2d414549adc75e0ba890257b
Source dataset
uspto-grants-2001_03
Patent number
US06197729B1

Reaction notes

Loading…