(+/-)-cis-1-[3,5-Bis(trifluoromethyl)benzoyl]-2-(phenylmethyl)-4-[4-(phenylmethyl)-1-piperazinyl]piperidine → (+/-)-1-[3,5-Bis(trifluoromethyl)benzoyl]-2-(phenylmethyl)-4-(1-piperazinyl)piperidine
Reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([N:14]2[CH2:19][CH2:18][N:17](CC3C=CC=CC=3)[CH2:16][CH2:15]2)[CH2:10][C@@H:9]1[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:7]>CO.[Pd]>[F:41][C:2]([F:1])([F:42])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:40])([F:38])[F:39])[CH:36]=1)[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)[CH2:10][CH:9]1[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:7]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of compound 16 (8.4 g) in methanol (250 ml) was hydrogenated at 50° C. with palladium on activated carbon (10%) (2 g) as a catalyst. After uptake of H2, the catalyst was filtered off and the filtrate was evaporated, yielding 7 g (100%) of (±)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(phenylmethyl)-4-(1-piperazinyl)piperidine (compound 15).
Workup
- filtrationAfter uptake of H2, the catalyst was filtered off
- customthe filtrate was evaporated
Sources & evidence
- ORD record
- ord-835433560d4746ba92a399144244acff
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06521621B1
Reaction notes
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