Water → 1-[2,4-Bis(trifluoromethyl)benzyl]-2-oxopiperidine-4-carboxylic acid
Reaction equation
[O:1]=[C:2]1[CH2:7][CH:6]([C:8]([OH:10])=[O:9])[CH2:5][CH2:4][NH:3]1.[H-].[Na+].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=1[C:25]([F:28])([F:27])[F:26].O>O1CCCC1>[F:26][C:25]([F:27])([F:28])[C:16]1[CH:17]=[C:18]([C:21]([F:24])([F:22])[F:23])[CH:19]=[CH:20][C:15]=1[CH2:14][N:3]1[CH2:4][CH2:5][CH:6]([C:8]([OH:10])=[O:9])[CH2:7][C:2]1=[O:1]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-oxopiperidine-4-carboxylic acid (21.3 g) in tetrahydrofuran (300 mL) was added 60% sodium hydride (18 g, containing mineral oil) under cooling to 0° C. The reaction mixture was stirred for 30 min under cooling to 0° C. To the reaction mixture was added dropwise 1-(bromomethyl)-2,4-bis(trifluoromethyl)benzene (46 g) under cooling to 0° C., and the mixture was further stirred at 80° C. for 2 days. Water was added to the reaction mixture under cooling to 0° C., and the mixture was extracted with ethyl acetate. To the aqueous layer was further added 10% hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was dried over sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (32 g).
Workup
- temperatureunder cooling to 0° C
- temperatureunder cooling to 0° C.
- stirringthe mixture was further stirred at 80° C. for 2 days
- temperatureunder cooling to 0° C.
- extractionthe mixture was extracted with ethyl acetate
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe extract was dried over sodium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-6f0cb7cf409f4b6da26145a8fe848f96
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772277B2
Reaction notes
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