2-(cis-2,6-Dimethyl-1-piperidinyl)ethanamine → Ammonia

HRID 1635627Notes

Reaction equation

HRID 1635627 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][C@H:20]1[CH2:25][CH2:24][CH2:23][C@@H:22]([CH3:26])[N:21]1[CH2:27][CH2:28][NH2:29]>>[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:29][CH2:28][CH2:27][N:21]1[C@H:22]([CH3:26])[CH2:23][CH2:24][CH2:25][C@@H:20]1[CH3:19])=[O:18]

Participants

4

Reactant 2

HCID 7837022-(cis-2,6-Dimethyl-1-piperidinyl)ethanamineHCID 12050655(2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acid

Product 2

HCID 222AmmoniaHCID 9843067HCID 9843067, compound

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-[(cis)-2,6-dimethyl-1-piperidinyl]ethylamine [J. Med. Chem., 27; 5, (1984), 684-691]. 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)-N2-2[(cis)-2,6-dimethyl-1-piperidinyl]ethyl-2-piperidinecarboxamide as a colourless gum.

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-487c5d702ff04a46bd0d219184dbd8a4
Source dataset
uspto-grants-2003_01
Patent number
US06509464B1

Reaction notes

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