Allyl bromide → 1-(Prop-2-en-1-yl)piperidin-2-one

HRID 359347Notes

Reaction equation

HRID 359347 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:7].[H-].[Na+].[CH2:10](Br)[CH:11]=[CH2:12]>CN(C=O)C>[CH2:12]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:7])[CH:11]=[CH2:10]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 126652-PiperidoneHCID 24758Sodium hydride

Product 1

HCID 130881971-(Prop-2-en-1-yl)piperidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Piperidinone is deprotonated with NaH in DMF solution and reaction with allyl bromide, and 1-allyl-2-piperidinone is obtained by distillation. Ozonolysis in MeOH solution at -78° C., followed by reductive workup with Me2S, gives the aldehyde derivative, which is reductively aminated using diethylamine hydrochloride and NaBH4 to give the title compound.

Sources & evidence

ORD record
ord-9995f42a8eb44850bf232e363e52f6ac
Source dataset
uspto-grants-1991_03
Patent number
US05001113

Reaction notes

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