O-Phenylenediamine → 2-[4-[4-(4-Phenyl-1-piperazinyl)-1-butynyl]phenyl]-1H-benzimidazole

HRID 375528Notes

Reaction equation

HRID 375528 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]#[C:16][C:17]3[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(O)[O-].[Na+].[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH2:37]>CO>[NH3:7].[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]#[C:16][C:17]3[CH:24]=[CH:23][C:20]([C:21]4[NH:37][C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=5[N:30]=4)=[CH:19][CH:18]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7243O-PhenylenediamineHCID 189930464-[4-(4-Phenylpiperazin-1-yl)but-1-ynyl]benzaldehydeHCID 23665763Sodium Bisulfite

Product 2

HCID 222AmmoniaHCID 189930372-[4-[4-(4-Phenyl-1-piperazinyl)-1-butynyl]phenyl]-1H-benzimidazoleYield 85.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-[4-(4-phenylpiperazin-1-yl)but-1-ynyl]benzaldehyde (Example B) (1.28 g), sodium bisulfite (0.4 g) and 1,2-diaminobenzene (0.43 g) is stirred in methanol (50 mL) at reflux for 18 hours. The mixture is filtered and the solvent evaporated. The residue is purified by chromatography on silica gel eluting with 200:8:1 dichloromethane:ethanol:0.880 aqueous ammonia to give 0.70 g of the title compound as a tan solid; mp 247°-248° C.

Workup

  1. temperatureat reflux for 18 hours
  2. filtrationThe mixture is filtered
  3. customthe solvent evaporated
  4. customThe residue is purified by chromatography on silica gel eluting with 200:8:1 dichloromethane

Sources & evidence

ORD record
ord-0be8c9b0f4e349d4932b1596cfacdb5a
Source dataset
uspto-grants-1996_01
Patent number
US05486517

Reaction notes

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