Chloride → Ethyl alpha-acetyl-4-(4-fluorobenzoyl)-1-piperidinepentanoate

HRID 66683Notes

Reaction equation

[H-].[Na+].[O:3]=[C:4]([CH3:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[Cl-].Cl[CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([C:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[O:24])[CH2:19][CH2:18]1>CC1C=CC=CC=1>[C:4]([CH:5]([CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([C:23](=[O:24])[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:19][CH2:18]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:11]

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirred mixture of 4 parts of a sodium hydride dispersion 60% in 180 parts of methylbenzene are added dropwise 12 parts of ethyl 3-oxobutanoate at room temperature. Then there is added 1 part of N,N,N-tridecylmethanammonium chloride and the whole is warmed to 40° C. At this temperature, a solution of 25 parts of [1-(3-chloropropyl)-4-piperidinyl](4-fluorophenyl)methanone in 45 parts of methylbenzene is added slowly. The whole is heated to reflux and stirring is continued overnight at reflux temperature. The reaction mixture is cooled to room temperature and filtered over Hyflo. The filtrate is evaporated, yielding 24 parts of ethyl α-acetyl-4-(4-fluorobenzoyl)-1-piperidinepentanoate as a residue.

Workup

temperatureThe whole is heated
temperatureto reflux
temperatureat reflux temperature
temperatureThe reaction mixture is cooled to room temperature
filtrationfiltered over Hyflo
customThe filtrate is evaporated

Sources & evidence

ORD record: ord-7ef74cc1425143db850e7a32adec9fe2
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04342870

Reaction notes

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