Water → 2-[4-(2,6-Dichlorophenyl)piperazin-1-yl]-6-trifluoromethyl-1H-benzoimidazole

HRID 730702

Reaction equation

HRID 730702 reaction equation
Cl[C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=[CH:10][C:4]=2[N:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(N(CC)C(C)C)(C)C.O>CS(C)=O>[Cl:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([Cl:15])[C:17]=1[N:23]1[CH2:28][CH2:27][N:26]([C:2]2[NH:6][C:5]3[CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=[CH:10][C:4]=3[N:3]=2)[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 3379052-chloro-6-(trifluoromethyl)-1H-benzimidazoleHCID 114923451-(2,6-Dichlorophenyl)piperazine

Product 1

HCID 100474472-[4-(2,6-Dichlorophenyl)piperazin-1-yl]-6-trifluoromethyl-1H-benzoimidazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of the benzoimidazole from step (c) above (75 mg, 0.34 mmol), the piperazine from step (a) above (90 mg, 0.39 mmol) and N,N-diisopropylethylamine (0.1 mL, 0.58 mmol, Aldrich) in DMSO (2 mL) was stirred at 80° C. for 24 h. The mixture was cooled to room temperature, water (10 mL) was added and the mixture was extracted with EtOAc (2×20 mL). The combined organic phases were washed with water (2×10 mL) and brine (5 mL), dried over Na2SO4, and filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 20% EtOAc/hexane to give the title compound as a white solid. M.p. 263-265° C. MS (ESI, pos. ion) m/z: 415 (M+1).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×20 mL)
  2. washThe combined organic phases were washed with water (2×10 mL) and brine (5 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by silica gel chromatography
  7. washeluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-18db05cfa2954c4b856ff9818bcadebf
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Linked notes

Loading…