Water → (4-Methylenepiperidin-1-yl)(phenyl)methanone

HRID 1005445Notes

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.C[O-].[Na+].C1(C)C=CC=CC=1.O>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 10 ml of N,N-dimethylformamide was dissolved 1.50 g (6.32 mmol) of N-benzoyl-4-chloromethylpiperidine (D). The resulting solution was cooled to 5° C. and thereto was added 1.36 g (25.28 mmol) of sodium methoxide. After stirring at 60° C. for 4 hours, the reaction mixture was cooled down to room temperature and then poured into a mixed liquid of 40 ml of toluene and 40 ml of iced water. An organic layer was separated and dried over 2 g of anhydrous magnesium sulfate and, thereafter, the solvent was removed by distillation. The residual liquid was subjected to silicagel column chromatography (stationary phase: 50 g of Silicagel 60 available from Merck KGaA). The fraction eluted with a hexane/ethyl acetate mixture (2:1 (v/v)) was collected. The solvent was removed by distillation from the obtained fraction to obtain 1.00 g of N-benzoyl-4-methylenepiperidine (E) as a colorless crystal. The NMR spectrum of this compound coincided with that of the product in Example 4.

Workup

temperaturethe reaction mixture was cooled down to room temperature
customAn organic layer was separated
dry with materialdried over 2 g of anhydrous magnesium sulfate
customthe solvent was removed by distillation
washThe fraction eluted with a hexane/ethyl acetate mixture (2:1 (v/v))
customwas collected
customThe solvent was removed by distillation from the obtained fraction

Sources & evidence

ORD record: ord-8e2dac9bf3764961838a81f3ebee373f
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06054586

Reaction notes

Loading…