Cyclobutylamine → (2-Cyclobutylamino-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

HRID 736243Notes

Reaction equation

HRID 736243 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)[CH2:16][CH2:15]1)=[O:13].[CH:30]1([NH2:34])[CH2:33][CH2:32][CH2:31]1>CC(N(C)C)=O>[CH:30]1([NH:34][C:2]2[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=2[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)[CH2:16][CH2:15]2)=[O:13])[CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 75645CyclobutylamineHCID 59793691(2-Iodo-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

Product 1

HCID 68843963(2-Cyclobutylamino-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanoneYield 54%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of (2-Iodo-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone (compound CK, 0.05 g, 0.09 mmol) and of cyclobutylamine (0.1 ml) in dimethylacetamide was heated in a microwave oven (180 deg) for 10 min before being concentrated in vacuo. The residue was dissolve in ethyl acetate, washed with water dried over sodiumsulfate, filtered and concentrated. The residue was purified by column chromatography (SiO2, 5 g, Heptane/EtOAc 0-50%) to give the title compound as a white foam (24 mg, 54%). MS (m/e): 482.5 (M+H+, 100%).

Workup

  1. concentrationbefore being concentrated in vacuo
  2. dissolutionThe residue was dissolve in ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodiumsulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (SiO2, 5 g, Heptane/EtOAc 0-50%)

Sources & evidence

ORD record
ord-f863a0af7ce641dba72ae2e29d212358
Source dataset
uspto-grants-2009_09
Patent number
US07595314B2

Reaction notes

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