Morpholine → rac4-(5-Methanesulfonyl-2-morpholin4-yl-benzoyl)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 32738Notes

Reaction equation

HRID 32738 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:26])[C:15]2[CH:20]=[C:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:18]=[CH:17][C:16]=2I)[CH:10]([CH3:27])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:26])[C:15]2[CH:20]=[C:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:18]=[CH:17][C:16]=2[N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:10]([CH3:27])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 59793735Rac-4-(2-iodo-5-methanesulfonyl-benzoyl)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59793661rac4-(5-Methanesulfonyl-2-morpholin4-yl-benzoyl)-3-methyl-piperazine-1-carboxylic acid tert-butyl esterYield 88%

Conditions

Temperature
100 °C

Procedure

rac-4-(2-Iodo-5-methanesulfonyl-benzoyl)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester (400 mg, 0.78 mmol) was poured into morpholine (5.0 ml) and the reaction mixture was stirred for 15 h at 100° C. before being concentrated in vacuo. The residue was then purified by column chromatography (SiO2, 20 g, dichloromethane/methanol=0-5%) to give the title compound as a colorless foam (322 mg, 88%). MS (m/e): 468.3 (M+H+).

Workup

  1. concentrationbefore being concentrated in vacuo
  2. customThe residue was then purified by column chromatography (SiO2, 20 g, dichloromethane/methanol=0-5%)

Sources & evidence

ORD record
ord-5b824d6ecda94347b3ebc4a13ac6c7a4
Source dataset
uspto-grants-2008_09
Patent number
US07427612B2

Reaction notes

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