Potassium Carbonate → (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[(E)-4-chloro-2-butenyl]piperazine

HRID 2288214Notes

Reaction equation

[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=1)=[O:7].[Cl:32][CH2:33]/[CH:34]=[CH:35]/[CH2:36]Cl.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:31][C:2]([F:1])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:25]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:36]/[CH:35]=[CH:34]/[CH2:33][Cl:32])[CH2:10][C@H:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=1)=[O:7]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine (1.0 g), (E)-1,4-dichloro-2-butene (0.31 ml) and powdered potassium carbonate (0.4 g) in dry acetonitrile (10 ml) was heated at 50° C. After 4 hours, the reaction mixture was cooled and then filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by column chromatography on silica gel using a mixture of toluene and ethyl acetate (4:1) to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[(E)-4-chloro-2-butenyl]piperazine (0.53 g) as an oil.

Workup

temperaturethe reaction mixture was cooled
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure
customthe resulting residue was purified by column chromatography on silica gel using
additiona mixture of toluene and ethyl acetate (4:1)

Sources & evidence

ORD record: ord-720a66dc63a84e3f8d371e9820020f01
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06087357

Reaction notes

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