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

HRID 2298836Notes

Reaction equation

HRID 2298836 reaction equation
[CH3:1][C:2]1[C:3]([CH3:20])=[CH:4][C:5]2[O:9][C:8]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]3[C:16]([OH:18])=O)=[N:7][C:6]=2[CH:19]=1.[CH3:21][C@H:22]1[CH2:27][CH2:26][CH2:25][C@@H:24]([CH3:28])[N:23]1[CH2:29][CH2:30][NH2:31]>>[CH3:21][C@H:22]1[CH2:27][CH2:26][CH2:25][C@@H:24]([CH3:28])[N:23]1[CH2:29][CH2:30][NH:31][C:16]([C@@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][N:10]1[C:8]1[O:9][C:5]2[CH:4]=[C:3]([CH3:20])[C:2]([CH3:1])=[CH:19][C:6]=2[N:7]=1)=[O:18].[NH3:7]

Participants

4

Reactant 2

HCID 7837022-(cis-2,6-Dimethyl-1-piperidinyl)ethanamineHCID 53784926HCID 53784926, compound

Product 2

HCID 222AmmoniaHCID 9844579HCID 9844579, compound

Procedure

The title compound was prepared by a similar method to Example 1 from (2S)-1-[5,6-dimethyl-1,3-benzoxazol-2-yl]-2-piperidinecarboxylic acid [see Preparation 53] 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 93:7:1, by volume, dichloromethane: methanol: 0.88 aqueous ammonia solution to afford (2S)-N-2-[(cis)-2,6-dimethyl-1-piperidinyl]ethyl-1-[1-(5,6-dimethyl-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 93:7:1, by volume, dichloromethane

Sources & evidence

ORD record
ord-85f0148e8ef44872bd5be64b11f447d6
Source dataset
uspto-grants-2002_12
Patent number
US06495549B1

Reaction notes

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