Carbon tetrabromide → Benzyl 3-(bromomethyl)piperidine-1-carboxylate

HRID 397678Notes

Reaction equation

HRID 397678 reaction equation
O[CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:4]1.C(Br)(Br)(Br)[Br:20]>>[Br:20][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:4]1

Participants

3

Reactant 2

HCID 11205Carbon tetrabromideHCID 2776577Benzyl 3-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 23000675Benzyl 3-(bromomethyl)piperidine-1-carboxylate

Procedure

The title compound was prepared by the method of Preparation 9 from benzyl 3-(hydroxymethyl)-1-piperidinecarboxylate [Preparation 59] and carbon tetrabromide. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 0:100 changing to 80:20, by volume ethyl acetate:hexane, in 10% increments, to afford benzyl 3-(bromomethyl)-1-piperidinecarboxylate as an oil.

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 0:100 changing to 80:20, by volume ethyl acetate

Sources & evidence

ORD record
ord-164ee47031954a3db82e5c0dac7edea4
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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