(2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acid → (2S)-1-(1,3-benzoxazol-2-yl)-N2-[2-(3,5-dimethylmorpholino)ethyl]-2-piperidinecarboxamide

HRID 1276151Notes

Reaction equation

HRID 1276151 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.[CH3:19][CH:20]1[N:25]([CH2:26][CH2:27][NH2:28])[CH:24]([CH3:29])[CH2:23][O:22][CH2:21]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:28][CH2:27][CH2:26][N:25]1[CH:24]([CH3:29])[CH2:23][O:22][CH2:21][CH:20]1[CH3:19])=[O:18]

Participants

3

Reactant 2

HCID 12050655(2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acidHCID 120961382-(3,5-Dimethylmorpholino)ethylamine

Product 1

HCID 9843166(2S)-1-(1,3-benzoxazol-2-yl)-N2-[2-(3,5-dimethylmorpholino)ethyl]-2-piperidinecarboxamide

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 2-(3,5-dimethylmorpholino)ethylamine [see Preparation 12]. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 changing to 95:5, by volume dichloromethane:methanol to afford (2S)-1-(1,3-benzoxazol-2-yl)-N2 -[2-(3,5-dimethylmorpholino)ethyl]-2-piperidinecarboxamide as a solid.

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 changing to 95:5, by volume dichloromethane

Sources & evidence

ORD record
ord-6e04c36176d540d58deb19feac561936
Source dataset
uspto-grants-2000_12
Patent number
US06166011

Reaction notes

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