Morpholine → morpholin-4-yl-{4-[(2S)-4-((1R)-1-phenylethyl)-morpholin-2-yl]-phenyl}-methanone

HRID 1091386Notes

Reaction equation

HRID 1091386 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]([OH:33])=O)=[CH:29][CH:28]=3)[CH2:22]2)[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>ClCCl>[N:36]1([C:31]([C:30]2[CH:34]=[CH:35][C:27]([C@@H:23]3[O:24][CH2:25][CH2:26][N:21]([C@@H:19]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH3:20])[CH2:22]3)=[CH:28][CH:29]=2)=[O:33])[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 665947974-[(2S)-4-((1R)-1-phenylethyl)-morpholin-2-yl]-benzoic acid

Product 1

HCID 66594396morpholin-4-yl-{4-[(2S)-4-((1R)-1-phenylethyl)-morpholin-2-yl]-phenyl}-methanoneYield 61.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1′-Carbonyldiimidazole (357 mg, 2.20 mmol) was added to a solution of 4-[(2S)-4-((1R)-1-phenylethyl)-morpholin-2-yl]-benzoic acid (623 mg, 2.00 mmol) in dichloromethane at 0° C. After stirring for 2 hours, morpholine (0.35 ml, 4.0 mmol) was added to the reaction mixture. After stirring over night, the resulting suspension was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to afford morpholin-4-yl-{4-[(2S)-4-((1R)-1-phenylethyl)-morpholin-2-yl]-phenyl}-methanone (465 mg, 60%.) as a colorless oil.

Workup

  1. stirringAfter stirring over night
  2. concentrationthe resulting suspension was concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-806be3a6e32446999c248b72eac1798b
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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