Benzyl Bromide → Ammonia

HRID 412647Notes

Reaction equation

HRID 412647 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[C:16]([NH:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:17].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[NH3:3].[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[C:16]([NH:18][CH:19]1[CH2:20][CH2:21][N:22]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:23][CH2:24]1)=[O:17]

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 57060556HCID 57060556, compound

Product 2

HCID 222AmmoniaHCID 57019504HCID 57019504, compound

Procedure

The title compound was prepared by a similar method to Example 6 from (2S)-1-(1,3-benzoxazol-2-yl)-N2-(4-piperidinyl)-2-piperidinecarboxamide [see Example 31] and benzyl bromide. The crude product was purified by column chromatography on silica gel eluting with a solvent system of 93:7:1, by volume, dichloromethane:methanol:0.88 aqueous ammonia solution to afford (2S)-1-(1,3-benzoxazol-2-yl)-N2-(1-benzyl-4-piperidinyl)-2-piperidinecarboxamide as an oil.

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent system of 93:7:1, by volume, dichloromethane

Sources & evidence

ORD record
ord-9adf4b798aab4d618ed870a645e0c7c9
Source dataset
uspto-grants-2003_05
Patent number
US06562964B1

Reaction notes

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