Hydrochloric Acid → (4-Methylenepiperidin-1-yl)(phenyl)methanone

HRID 1005442Notes

Reaction equation

[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([CH2:15]Cl)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Cl.C1(C)C=CC=CC=1>CN(C)C=O>[C:1]([N:9]1[CH2:14][CH2:13][C:12](=[CH2:15])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 5 °C

Procedure

In 1 l of N,N-dimethylformamide was dissolved 248.96 g (about 1 mol) of N-benzoyl-4-chloromethyl-piperidine (D) obtained in Example 3. The resulting solution was cooled to 5° C. and thereto was added 168.32 g (1.5 mol) of potassium tert-butoxide in five portions at 10° to 20° C. over about 1 hour. After the addition, the mixture was stirred at 10° to 20° C. for 40 minutes. Then, the reaction mixture was poured into a mixed liquid of 500 ml of 1N hydrochloric acid and 500 g of fragmentary ice. Subsequently, thereto was added 200 ml of toluene to separate an organic layer. The aqueous layer was extracted with 200 ml of toluene and the organic layers were combined. The combined organic layer was washed with 500 ml of water. The solvent was removed by distillation under reduced pressure to obtain 193.78 g of N-benzoyl-4-methylenepiperidine (E) as a yellowish brown oily matter. The NMR spectrum of the obtained compound was measured. The result is shown below.

Workup

additionAfter the addition
customto separate an organic layer
extractionThe aqueous layer was extracted with 200 ml of toluene
washThe combined organic layer was washed with 500 ml of water
customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record: ord-8610586b1b2a4529914507c847945d63
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06054586

Reaction notes

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