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

HRID 483873

Reaction equation

HRID 483873 reaction equation
[Br-].[N:2]1[CH:7]=[CH:6][CH:5]=[N:4][C:3]=1[N:8]1[CH2:17][CH2:16][N+:11]2([CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:10][CH2:9]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:4]1[CH:5]=[CH:6][CH:7]=[N:2][C:3]=1[N:8]1[CH2:9][CH2:10][N:11]([CH2:15][CH2:14][CH2:13][CH2:12][N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[N:20]=[CH:19]2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 6575058-Aza-5-azoniaspiro(4.5)decane, 8-(2-pyrimidinyl)-, bromide (1:1)

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 450 g (1.50 moles) of 8-(2-pyrimidinyl)-8-aza-5-azoniaspiro[4,5]decane bromide, 177 g (1.50 moles) of benzimidazole and 307 g (2.25 moles) of potassium carbonate in 2 l of dimethylformamide is heated to 140°-145° C. for 14 hours. The mixture is evaporated under vacuum, chloroform is added, the solution is washed with water, dried over sodium sulfate and evaporated under vacuum, and 457 g (91%) of 1-{4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl}-1H-benzimidazole, with a melting point of 85°-88° C., are obtained.

Workup

  1. temperatureis heated to 140°-145° C. for 14 hours
  2. customThe mixture is evaporated under vacuum, chloroform
  3. additionis added
  4. washthe solution is washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under vacuum, and 457 g (91%) of 1-{4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl}-1H-benzimidazole, with a melting point of 85°-88° C.
  7. customare obtained

Sources & evidence

ORD record
ord-7d45aa6c12ef49eeba4c69f783581040
Source dataset
uspto-grants-1993_07
Patent number
US05227486

Linked notes

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