Water → HCID 25189209, compound

HRID 2065762Notes

Reaction equation

HRID 2065762 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[CH2:16][CH2:15][NH:14][CH:13]([C:17]([N:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:26]=4[CH3:32])[CH2:21][CH2:20]3)=[O:18])[CH2:12]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:40][CH2:41][CH3:42].O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([CH2:40][CH2:41][CH3:42])[CH:13]([C:17]([N:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:26]=4[CH3:32])[CH2:21][CH2:20]3)=[O:18])[CH2:12]2)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 10796Cesium carbonateHCID 68729707HCID 68729707, compound

Product 1

HCID 25189209HCID 25189209, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of [4-(3-chloro-benzenesulfonyl)-piperazin-2-yl]-[4-(2,5-dimethyl-phenyl)-piperazin-1-yl]-methanone (100 mg) in acetone (4 mL) was added cesium carbonate (82 mg), followed by 1-bromopropane (21 μL). The reaction mixture was stirred at reflux overnight. Water was added and the reaction mixture was extracted with ethyl acetate (×2). The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated. Purification by chromatography (SiO2, n-heptane/ethyl acetate 3:1) yielded [4-(3-chloro-benzenesulfonyl)-1-propyl-piperazin-2-yl]-[4-(2,5-dimethyl-phenyl)-piperazin-1-yl]-methanone as a white foam (75 mg), MS: 519.3 ([M+H, 1Cl]+).

Workup

  1. temperatureat reflux overnight
  2. extractionthe reaction mixture was extracted with ethyl acetate (×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography (SiO2, n-heptane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-1d4f5d9bc40942c2a35f7d50646c3e26
Source dataset
uspto-grants-2012_10
Patent number
US08288541B2

Reaction notes

Loading…