Benzyl Bromide → (3S)-N,N-Dimethyl-1-(phenylmethyl)-3-piperidinecarboxamide

HRID 432832Notes

Reaction equation

HRID 432832 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([O:16]CC)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][N:20](C)[C:21]([C@H]1CCCNC1)=O.C(N(C(C)C)CC)(C)C.C(Br)C1C=CC=CC=1>>[CH3:19][N:20]([CH3:21])[C:14]([C@H:10]1[CH2:11][CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1)=[O:16]

Participants

5

Reactant 4

HCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 2736370ethyl 1-benzylpiperidine-3-carboxylateHCID 11469201HCID 11469201, compound

Product 1

HCID 53939102(3S)-N,N-Dimethyl-1-(phenylmethyl)-3-piperidinecarboxamide

Procedure

This reaction was run in the same manner as ethyl 1-benzyl-3-piperidinecarboxylate, starting with (S)-N,N-dimethyl-3-piperidinecarboxamide (275 mg; 1.76 mmol), diisopropylethylamine (310 μl; 1.78 mmol), and benzyl bromide (210 μl; 1.77 mmol). Crude product was purified by chromatography on silica eluting with 5% methanol/95% dichloromethane, giving (S)-N,N-dimethyl 1-benzyl-3-piperidinecarboxamide (322.2 mg) as a colorless oil. MS m/z (positive ion) 247 (MH+; 100).

Workup

  1. customCrude product was purified by chromatography on silica eluting with 5% methanol/95% dichloromethane

Sources & evidence

ORD record
ord-b43686dc6f464276995c3fc6fcfe36de
Source dataset
uspto-grants-2003_12
Patent number
US06664271B1

Reaction notes

Loading…