Triethylamine → 1-(2-Ethylbutyryl)piperidin-4-one

HRID 552326Notes

Reaction equation

C(N(CC)CC)C.Cl.[NH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=O.[CH2:16]([CH:18]([CH2:22][CH3:23])[C:19](Cl)=[O:20])[CH3:17].[OH-:24].[K+]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:16]([CH:18]([CH2:22][CH3:23])[C:19]([N:9]1[CH2:14][CH2:13][C:12](=[O:24])[CH2:11][CH2:10]1)=[O:20])[CH3:17]

Participants

Conditions

Temperature: -10 °C

Procedure

Triethylamine (5.8 g, 57.3 mmol) and a catalytic amount of DMAP were added to a solution of piperidone hydrochloride (4.0 g, 26 mmol) in CH2Cl2 (20 ml). After cooling to −10° C., 2-ethylbutyryl chloride (3.9 g, 28.6 mmol) dissolved in CH2Cl2 (10 ml) was slowly added and the mixture was stirred at RT for 16 h. 5M potassium hydroxide solution (25 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-(2-ethylbutyryl)piperidin-4-one was obtained in a yield of 4.3 g (84% of theory).

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-d8be83b15251499db356120b356c60bd
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951815B2

Reaction notes

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