Benzyl Bromide → 1-Benzyl-4,4-dimethylpiperidine-2,6-dione

HRID 2191575Notes

Reaction equation

[CH3:1][C:2]1([CH3:10])[CH2:7][C:6](=[O:8])[NH:5][C:4](=[O:9])[CH2:3]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH2:18]([N:5]1[C:6](=[O:8])[CH2:7][C:2]([CH3:10])([CH3:1])[CH2:3][C:4]1=[O:9])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4,4-dimethylpiperidine-2,6-dione (2.0 g, 14.2 mmol) in acetone (50 mL) was added K2CO3 (3.92 g, 28.3 mmol) followed by (bromomethyl)benzene (1.85 mL, 15.6 mmol). The reaction mixture was heated at 50° C. for 4 h then cooled to room temperature and stirred overnight. The thick white precipitate present was removed via filtration, rinsing with acetone. The filtrate was concentrated and purified by SiO2 chromatography (10% to 50% EtOAc/hexanes) to afford 3.0 g (92%) of 1-benzyl-4,4-dimethylpiperidine-2,6-dione as a white solid.

Workup

temperaturethen cooled to room temperature
customThe thick white precipitate present was removed via filtration
washrinsing with acetone
concentrationThe filtrate was concentrated
custompurified by SiO2 chromatography (10% to 50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-766bb669f1944800a1540280617e7be0
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329699B2

Reaction notes

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