Sodium Carbonate → 1-(4-Methylpiperazin-1-yl)-3-(3-phenyl-6-trifluoromethyl-3H-benzimidazol-4-yl)prop-2-en-1-one

HRID 644541Notes

Reaction equation

HRID 644541 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[CH3:5][N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.C[O:13][C:14](=O)[CH:15]=[CH:16][C:17]1[C:25]2[N:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:23]=[N:22][C:21]=2[CH:20]=[C:19]([C:32]([F:35])([F:34])[F:33])[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:5][N:6]1[CH2:11][CH2:10][N:9]([C:14](=[O:13])[CH:15]=[CH:16][C:17]2[C:25]3[N:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:23]=[N:22][C:21]=3[CH:20]=[C:19]([C:32]([F:34])([F:33])[F:35])[CH:18]=2)[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 531671-MethylpiperazineHCID 6451240Aluminum(III) ChlorideHCID 674849573-(3-Phenyl-6-trifluoromethyl-3H-benzimidazol-4-yl)acrylic acid methyl ester

Product 1

HCID 674849301-(4-Methylpiperazin-1-yl)-3-(3-phenyl-6-trifluoromethyl-3H-benzimidazol-4-yl)prop-2-en-1-oneYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of aluminium trichloride (1.46 mmol, 195 mg) in dichloromethane (3 ml) was added dropwise N-methylpiperazine (1.83 mmol, 203 l). The resultant mixture was stirred for 0.5 h and to this, a solution of 3-(3-phenyl-6-trifluoromethyl-3H-benzimidazol-4-yl)acrylic acid methyl ester (0.73 mmol, 250 mg) was added dropwise. The resultant mixture stirred for 16 h at 60° C. Upon cooling, aqueous sodium carbonate (5%, 5 ml) was added and the mixture was shaken. The organic layer was isolated by filtration through a hydrophobic frit and evaporated under reduced pressure to give an off-white solid. Recrystallisation from diethyl ether afforded the title compound as a white powder (160 mg, 53%), m/z 415.2 (M+H)+.

Workup

  1. temperatureUpon cooling
  2. customThe organic layer was isolated by filtration through a hydrophobic frit
  3. customevaporated under reduced pressure
  4. customto give an off-white solid
  5. customRecrystallisation from diethyl ether

Sources & evidence

ORD record
ord-d8fa7c8da0334e4581ae61a1b2d3b0b6
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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