Benzyl Bromide → 1-benzyl-N-methoxy-N-methylpiperidine-4-carboxamide

HRID 555795Notes

Reaction equation

[CH3:1][O:2][N:3]([CH3:12])[C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:13]([N:9]1[CH2:8][CH2:7][CH:6]([C:4]([N:3]([O:2][CH3:1])[CH3:12])=[O:5])[CH2:11][CH2:10]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To the solution of N-methoxy-N-methylpiperidine-4-carboxamide (40 g, 232 mmol) in acetone (400 mL) was added benzyl bromide (42 mL, 349 mmol) and K2CO3 (64 g, 465 mmol) and the reaction mixture was stirred at 80° C. under reflux for 16 h. After completion of the reaction, the reaction mixture was filtered and acetone was removed under reduced pressure. The residue was purified by silica gel column chromatography (eluting with 50% ethyl acetate in hexane) to afford 1-benzyl-N-methoxy-N-methylpiperidine-4-carboxamide product. [M+1]=263.15

Workup

temperatureunder reflux for 16 h
customAfter completion of the reaction
filtrationthe reaction mixture was filtered
customacetone was removed under reduced pressure
customThe residue was purified by silica gel column chromatography (eluting with 50% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-423421afcf784d10b678fc366786b729
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053438B2

Reaction notes

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