Benzimidazole → HCID 19802565, compound

HRID 1645818Notes

Reaction equation

HRID 1645818 reaction equation
[H-].[Na+].[N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][CH:4]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25][CH2:24][N:23]([C:26](=[O:35])[CH:27](Cl)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:22][CH2:21]1>CN(C)C=O>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:21][CH2:22][N:23]([C:26](=[O:35])[CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:3]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[N:5]=[CH:4]2)[CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 24758Sodium hydrideHCID 3622053Piperazine, 1-(chlorophenylacetyl)-4-(2-methoxyphenyl)-

Product 1

HCID 19802565HCID 19802565, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of sodium hydride (0.47 g of 80% dispersion) in dry dimethyl formamide (10 ml) at 0°-5° C. was treated with benzimidazole (1.584 g) and the mixture stirred for 30 mins. A solution of 1-(2-methoxyphenyl)-4-(2-chloro-1-oxo-2-phenylethyl) piperazine (4.624 g) in dry DMF (20 ml) was added and the mixture was stirred at 90° C. for 5 hrs then at ambient temperature overnight. The suspension was filtered and the solvent evaporated under vacuum. The residue, in dichloromethane was washed well with water and dried over magnesium sulphate, to give 6 g of an oil. The crude product was purified by dry column flash chromatography to give the title compound (2.4 g).

Workup

  1. stirringthe mixture was stirred at 90° C. for 5 hrs
  2. customat ambient temperature
  3. customovernight
  4. filtrationThe suspension was filtered
  5. customthe solvent evaporated under vacuum
  6. washThe residue, in dichloromethane was washed well with water
  7. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-be3379d4c18041ddbf565b75de8e87dd
Source dataset
uspto-grants-1993_01
Patent number
US05177078

Reaction notes

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