1-Benzylpiperidin-3-amine → (2S)-1-(1,3-benzoxazol-2-yl)-N2-(1-benzyl-3-piperidinyl)hexahydro-2-pyridinecarboxamide

HRID 841927Notes

Reaction equation

HRID 841927 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]([OH:18])=O.[CH2:19]([N:26]1[CH2:31][CH2:30][CH2:29][CH:28]([NH2:32])[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[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:32][CH:28]1[CH2:29][CH2:30][CH2:31][N:26]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:27]1)=[O:18]

Participants

3

Reactant 2

HCID 4216941-Benzylpiperidin-3-amineHCID 12050655(2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acid

Product 1

HCID 9888286(2S)-1-(1,3-benzoxazol-2-yl)-N2-(1-benzyl-3-piperidinyl)hexahydro-2-pyridinecarboxamide

Procedure

The title compound was prepared by a similar method to Example 1 from (2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acid [see Preparation 3] and 1-benzyl-3-piperidinylamine [see J. Med. Chem. (1980), 23(8), 848-851]. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 90:10 changing to 40:60, by volume, hexane:ethyl acetate in 10% increments, to afford (2S)-1-(1,3-benzoxazol-2-yl)-N2-(1-benzyl-3-piperidinyl)hexahydro-2-pyridinecarboxamide as a yellow gum.

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 90:10 changing to 40:60, by volume, hexane

Sources & evidence

ORD record
ord-8ec5e4177ad74ab28df5d58935fe9c80
Source dataset
uspto-grants-2002_04
Patent number
US06372736B1

Reaction notes

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