Water → HCID 25185066, compound

HRID 2065764Notes

Reaction equation

HRID 2065764 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][NH:15][CH:14]([C:18]([N:20]3[CH2:25][CH2:24][N:23]([C:26]4[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][C:27]=4[CH3:33])[CH2:22][CH2:21]3)=[O:19])[CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:41][CH2:42][CH2:43][CH2:44][CH3:45].O>CC(C)=O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH:14]([C:18]([N:20]3[CH2:21][CH2:22][N:23]([C:26]4[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][C:27]=4[CH3:33])[CH2:24][CH2:25]3)=[O:19])[CH2:13]2)(=[O:10])=[O:11])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80571-Bromopentane2×HCID 10796Cesium carbonate2×HCID 68728970HCID 68728970, compound

Product 1

HCID 25185066HCID 25185066, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of [4-(4-chloro-benzenesulfonyl)-piperazin-2-yl]-[4-(2,5-dimethyl-phenyl)-piperazin-1-yl]-methanone hydrochloride (100 mg) in acetone (4 mL) was added cesium carbonate (254 mg), followed by 1-bromopentane (27 μL). The reaction mixture was stirred at ambient temperature for 1 h. Additional cesium carbonate (127 mg) and 1-bromopentane (14 μL) were added and stirring was continued at reflux over night. 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-(4-chloro-benzenesulfonyl)-1-pentyl-piperazin-2-yl]-[4-(2,5-dimethyl-phenyl)-piperazin-1-yl]-methanone as a white foam, MS: 547.3 ([M+H, 1Cl]+).

Workup

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

Sources & evidence

ORD record
ord-b410e58ebf99486d810cc2a60b8d5272
Source dataset
uspto-grants-2012_10
Patent number
US08288541B2

Reaction notes

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