Morpholine → Rac-(5-methanesulfonyl-2-morpholin-4-yl-phenyl)-[3-methyl-4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

HRID 736206Notes

Reaction equation

HRID 736206 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[CH:16]([CH3:30])[CH2:15]1)=[O:13].[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>>[CH3:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[C:3]([C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)[CH:16]([CH3:30])[CH2:15]2)=[O:13])[CH:4]=1)(=[O:10])=[O:9]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 59793688(2-Iodo-5-methanesulfonyl-phenyl)-[3-methyl-4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

Product 1

HCID 68840236Rac-(5-methanesulfonyl-2-morpholin-4-yl-phenyl)-[3-methyl-4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanoneYield 94%

Conditions

Temperature
100 °C

Procedure

(2-Iodo-5-methanesulfonyl-phenyl)-[3-methyl-4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone (50 mg, 0.09 mmol) was poured into morpholine (2.0 ml) and the reaction mixture was stirred for 24 h at 100° C. before being concentrated in vacuo. The residue was then purified by column chromatography (SiO2, 20 g, Heptane/EtOAc 0-100%) to give the title compound as a light brown solid (43.5 mg, 94%). MS (m/e): 512.3 (M+H+).

Workup

  1. concentrationbefore being concentrated in vacuo
  2. customThe residue was then purified by column chromatography (SiO2, 20 g, Heptane/EtOAc 0-100%)

Sources & evidence

ORD record
ord-9ac6abddc41f48e282b3d58af0a46f19
Source dataset
uspto-grants-2009_09
Patent number
US07595314B2

Reaction notes

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