Ethanolamine → N-(2-hydroxy-ethyl)-4-[(2S)-4-((1R)-1-phenyl-ethy)-morpholin-2-yl]-benzamide

HRID 424441Notes

Reaction equation

HRID 424441 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]1([C@H:19]([N:21]2[CH2:26][CH2:25][O:24][C@@H:23]([C:27]3[CH:35]=[CH:34][C:30]([C:31](O)=[O:32])=[CH:29][CH:28]=3)[CH2:22]2)[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:36]([CH2:38][NH2:39])[OH:37]>ClCCl>[OH:37][CH2:36][CH2:38][NH:39][C:31](=[O:32])[C:30]1[CH:34]=[CH:35][C:27]([C@@H:23]2[O:24][CH2:25][CH2:26][N:21]([C@@H:19]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH3:20])[CH2:22]2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 682631,1'-CarbonyldiimidazoleHCID 665947974-[(2S)-4-((1R)-1-phenylethyl)-morpholin-2-yl]-benzoic acid

Product 1

HCID 66704041N-(2-hydroxy-ethyl)-4-[(2S)-4-((1R)-1-phenyl-ethy)-morpholin-2-yl]-benzamideYield 73.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1′-Carbonyldiimidazole (540 mg, 3.30 mmol) was added to a solution of 4-[(2S)-4-((1R)-1-phenyl-ethy)-morpholin-2-yl]-benzoic acid (944 mg, 3.03 mmol) in dichloromethane at 0° C. After stirring for 2 hours, ethanolamine (0.36 ml, 6.0 mmol) was added to the reaction mixture and the mixture was stirred over night. The resulting suspension was concentrated in vacuo and the residue was purified by silica gel chromatography (ethyl acetate-hexane) to afford N-(2-hydroxy-ethyl)-4-[(2S)-4-((1R)-1-phenyl-ethy)-morpholin-2-yl]-benzamide (789 mg, 73%.) as a colorless oil.

Workup

  1. stirringthe mixture was stirred over night
  2. concentrationThe resulting suspension was concentrated in vacuo
  3. customthe residue was purified by silica gel chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-3a91221221b245da8a88fee6f4804867
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

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