1-Benzyl-4-piperidone → 1-Benzyl-4-(4-trifluoromethoxybenzylidene)piperidine
Reaction equation
[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)C=CC=CC=1.[H-].[Na+].[CH2:35]([N:42]1[CH2:47][CH2:46][C:45](=O)[CH2:44][CH2:43]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CS(C)=O>[CH2:35]([N:42]1[CH2:47][CH2:46][C:45](=[CH:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][C:17]([F:18])([F:19])[F:20])=[CH:14][CH:15]=2)[CH2:44][CH2:43]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1Participants
Procedure
Triphenyl-(4-trifluoromethoxybenzyl) phosphonium bromide (21.6 g, 41.75 mmol) was dissolved in DMSO (110 ml), to which sodium hydride (1.82 g, 45.52 mmol) was added, and the mixture was stirred for 30 minutes. 1-Benzyl-4-piperidone (7.18 g, 37.96 mmol) was added to the mixture, and the resulting mixture was stirred at 60° C. for 2 hours. The reaction mixture was poured into ice water, and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=10/1) to afford 1-benzyl-4-(4-trifluoromethoxybenzylidene)piperidine (9.75 g, yield 74%) as a yellow oil.
Workup
- additionwas added
- stirringthe resulting mixture was stirred at 60° C. for 2 hours
- extractionextracted with ethyl acetate
- washThe extract was washed with brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=10/1)
Sources & evidence
- ORD record
- ord-6a0d37c612ae496d952aeca889c33e88
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07262212B2
Reaction notes
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