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

HRID 2119405Notes

Reaction equation

HRID 2119405 reaction equation
[C:1]([O:4][C:5]1[CH:22]=[CH:21][C:8]2[N:9]=[C:10]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]3[C:18](O)=[O:19])[O:11][C:7]=2[CH:6]=1)(=[O:3])[CH3:2].[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]>>[NH3:9].[C:1]([O:4][C:5]1[CH:22]=[CH:21][C:8]2[N:9]=[C:10]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]3[C:18]([NH:33][CH2:32][CH2:31][N:25]3[C@H:26]([CH3:30])[CH2:27][CH2:28][CH2:29][C@@H:24]3[CH3:23])=[O:19])[O:11][C:7]=2[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7837022-(cis-2,6-Dimethyl-1-piperidinyl)ethanamineHCID 54274534HCID 54274534, compound

Product 2

HCID 222AmmoniaHCID 12096149HCID 12096149, compound

Procedure

The title compound was prepared by a similar method to Example 1 from (2S)-1-[6-(acetyloxy)-1,3-benzoxazol-2-yl]-2-piperidinecarboxylic acid [see Preparation 37] 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 99.4:1.4:0.2, by volume, dichloromethane:methanol:0.88 aqueous ammonia solution, to afford 2-[(2S)-2-[(2-[(cis)-2,6-dimethyl-1-piperidinyl]ethylamino)carbonyl]-1-piperidinyl]-1,3-benzoxazol-6-yl acetate as a white foam.

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0:0 changing to 99.4:1.4:0.2, by volume, dichloromethane

Sources & evidence

ORD record
ord-1bf54731bf184942b5e78b85b450d201
Source dataset
uspto-grants-2004_02
Patent number
US06686357B1

Reaction notes

Loading…