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

HRID 2298835Notes

Reaction equation

HRID 2298835 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[O:12][C:11]([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]3[C:20]([OH:22])=O)=[N:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[CH3:23][C@H:24]1[CH2:29][CH2:28][CH2:27][C@@H:26]([CH3:30])[N:25]1[CH2:31][CH2:32][NH2:33]>>[NH3:10].[CH3:23][C@H:24]1[CH2:29][CH2:28][CH2:27][C@@H:26]([CH3:30])[N:25]1[CH2:31][CH2:32][NH:33][C:20]([C@@H:15]1[CH2:16][CH2:17][CH2:18][CH2:19][N:14]1[C:11]1[O:12][C:13]2[C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=[CH:8][C:9]=2[N:10]=1)=[O:22]

Participants

4

Reactant 2

HCID 7837022-(cis-2,6-Dimethyl-1-piperidinyl)ethanamineHCID 54520364HCID 54520364, compound

Product 2

HCID 222AmmoniaHCID 12096153HCID 12096153, compound

Procedure

The title compound was prepared by a similar method to Example 1 from (2S)-1-[7-(methoxy)carbonyl-1,3-benzoxazol-2-yl]-2-piperidinecarboxylic acid [see Preparation 51] 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 gradient of 100:0:0 changing to 99:1:0 then 80:20:10, by volume, dichloromethane:methanol: 0.88 aqueous ammonia solution to afford (2S)-N-2-[(cis)-2,6-dimethyl-1-piperidinyl]ethyl-1-[7-(methoxy)carbonyl-1,3-benzoxazol-2-yl]-2-piperidinecarboxamide as a white solid.

Workup

  1. customThe crude product was purified by column chromatography on silica gel
  2. washeluting with a solvent gradient of 100:0:0 changing to 99:1:0

Sources & evidence

ORD record
ord-acc628d9a530499381dd87d38586e4bb
Source dataset
uspto-grants-2002_12
Patent number
US06495549B1

Reaction notes

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