Acetic Acid → methyl [1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1H-benzimidazol-2-yl]carbamate

HRID 354995Notes

Reaction equation

HRID 354995 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][N:15]([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH2:13]1.[CH3:31][O:32][C:33](=[O:39])[NH:34][CH2:35]OC=N.C(O)(=O)C>ClC(Cl)Cl>[C:19]1([CH:18]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:15]2[CH2:14][CH2:13][N:12]([CH2:11][CH2:10][CH2:9][N:8]3[C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[N:1]=[C:35]3[NH:34][C:33](=[O:39])[O:32][CH3:31])[CH2:17][CH2:16]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 13105609N~1~-{3-[4-(Diphenylmethyl)piperazin-1-yl]propyl}benzene-1,2-diamineHCID 15037334Methyl (iminomethoxymethyl)-carbamate

Product 1

HCID 13105584methyl [1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1H-benzimidazol-2-yl]carbamate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 60 parts of N-(2-aminophenyl)-4-(diphenylmethyl)-1-piperazinepropanamine, 20 parts of methyl(iminomethoxymethyl)carbamate, 42 parts of acetic acid and 450 parts of trichloromethane is stirred and refluxed overnight. The reaction mixture is evaporated and the residue is stirred in water. The latter is decanted and the residue is taken up again in water. The whole is alkalized with a diluted ammonium hydroxide solution and the product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane, yielding methyl [1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1H-benzimidazol-2-yl]carbamate; mp. 137.8° C.

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture is evaporated
  3. stirringthe residue is stirred in water
  4. customThe latter is decanted
  5. extractionthe product is extracted with trichloromethane
  6. customThe extract is dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated
  13. customThe residue is crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-68bf4fc76ecb410cb077e1201645eef8
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Reaction notes

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