Benzimidazole → 1-{4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl}-1H-benzimidazole

HRID 1769611Notes

Reaction equation

HRID 1769611 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH2:8][CH2:7]1.[N:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[NH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:13]1[CH:14]=[CH:15][CH:16]=[N:17][C:12]=1[N:9]1[CH2:10][CH2:11][N:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[N:20]=[CH:19]2)[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 147268432-(4-(4-Bromobutyl)piperazin-1-yl)pyrimidine

Product 1

HCID 98191481-{4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl}-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6 g (20 mmol) of 2-[4-(4-bromobutyl)-1-piperazinyl]-pyrimidine, 2.36 g (20 mmol) of benzimidazole and 4.1 g (30 mmol) of potassium carbonate in 60 ml of dimethylformamide is refluxed for 14 hours. The reaction mixture is evaporated under vacuum, chloroform is added, the mixture is washed with water, dried over sodium sulphate and evaporated under vacuum and 4.8 g of 1-{4-[4-(2-pyrimidinyl)-1-piperazinyl]-butyl}-1H-benzimidazole are obtained, which may be recrystallised from ethyl ether, with a melting point of 85°-88° C.

Workup

  1. temperatureis refluxed for 14 hours
  2. customThe reaction mixture is evaporated under vacuum, chloroform
  3. additionis added
  4. washthe mixture is washed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated under vacuum and 4.8 g of 1-{4-[4-(2-pyrimidinyl)-1-piperazinyl]-butyl}-1H-benzimidazole
  7. customare obtained
  8. customwhich may be recrystallised from ethyl ether, with a melting point of 85°-88° C.

Sources & evidence

ORD record
ord-bb9f9015a0814603b73a671f894d6868
Source dataset
uspto-grants-1995_01
Patent number
US05382586

Reaction notes

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