4-Methylmorpholine → Ammonia

HRID 2298823Notes

Reaction equation

HRID 2298823 reaction equation
C[N:2]1CCOCC1.[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[C:23]([OH:25])=O.O.OC1C2N=NNC=2C=CC=1.[N:37]1([CH2:43][CH2:44][NH2:45])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.Cl.CN(C)CCCN=C=NCC>ClCCl.O>[NH3:2].[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[C:23]([NH:45][CH2:44][CH2:43][N:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1)=[O:25]

Participants

9

Reactant 5

HCID 79724-MethylmorpholineHCID 33944N-(2-Aminoethyl)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12050655(2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acidHCID 178526939HCID 178526939, compound

Product 2

HCID 222AmmoniaHCID 9820082HCID 9820082, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

N-methylmorpholine (0.085 ml) was added to a solution of (2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acid (95.5 mg) [see Preparation 3], hydroxybenzotriazole hydrate (89.0 mg), 2-piperidinoethylamine (50 mg) [see J. Chem. Soc, (1935), 1421-1426] and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (140 mg) in dichloromethane (20 ml). The reaction mixture was stirred at room temperature for 18 hours, after which time the mixture was diluted with water and the organic layer was separated, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 4:1:0, changing to 0:95:5, by volume, hexane:ethyl acetate: 0.88 aqueous ammonia solution solution to afford (2S)-1-(1,3-benzoxazol-2-yl)-N2-(2-piperidinoethyl)-2-piperidinecarboxamide (109 mg) as a white solid.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over magnesium sulphate
  3. customthe solvent removed under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 4:1:0

Sources & evidence

ORD record
ord-c790b32c243c43468458890fa231a73e
Source dataset
uspto-grants-2002_12
Patent number
US06495549B1

Reaction notes

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