Triethylamine → 1-(4-Chlorobenzoyl)piperidin-4-one

HRID 552327Notes

Reaction equation

C(N(CC)CC)C.Cl.[NH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=O.[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1.[OH-:26].[K+]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([N:9]2[CH2:14][CH2:13][C:12](=[O:26])[CH2:11][CH2:10]2)=[O:22])=[CH:19][CH:18]=1

Participants

Conditions

Temperature: -10 °C

Procedure

Triethylamine (4.4 g, 43.0 mmol) and a catalytic amount of DMAP were added to a solution of piperidone hydrochloride (3.0 g, 19.5 mmol) in CH2Cl2 (20 ml). After cooling to −10° C., 4-chlorobenzoyl chloride (3.8 g, 21.5 mmol) dissolved in CH2Cl2 (10 ml) was slowly added and the mixture was stirred at RT for 16 h. 5M potassium hydroxide solution (20 ml) was added to the suspension, the organic phase was separated off and the aqueous phase was extracted with CH2Cl2 (3×10 ml). After drying of the combined organic phases over Na2SO4, filtration and removal of the solvent, the product 1-(4-chlorobenzoyl)piperidin-4-one was obtained in a yield of 4.4 g (95%).

Workup

additionwas slowly added
customthe organic phase was separated off
extractionthe aqueous phase was extracted with CH2Cl2 (3×10 ml)
dry with materialAfter drying of the combined organic phases over Na2SO4, filtration and removal of the solvent

Sources & evidence

ORD record: ord-87c0fc6e837843ed8d545f17ddb2f652
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951815B2

Reaction notes

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