Acetic Acid → {1-butyl-5-[4-(diphenylmethyl)-1-piperazinylmethyl]-1H-benzimidazol-2-ylmethyl}acetate

HRID 1389316Notes

Reaction equation

HRID 1389316 reaction equation
[CH2:1]([NH:5][C:6]1[C:7]([NH2:32])=[CH:8][C:9]([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4].Cl.O[CH2:35][C:36](=N)[O:37][CH2:38][CH3:39].C(O)(=[O:43])C>>[CH2:1]([N:5]1[C:6]2[CH:11]=[CH:10][C:9]([CH2:12][N:13]3[CH2:18][CH2:17][N:16]([CH:19]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:15][CH2:14]3)=[CH:8][C:7]=2[N:32]=[C:39]1[CH2:38][O:37][C:36](=[O:43])[CH3:35])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 12383662Ethyl 2-hydroxyacetimidate hydrochlorideHCID 131712028N1-butyl-4-[4(diphenylmethyl)-1-piperazinylmethyl]-1,2-benzenediamine

Product 1

HCID 131712027{1-butyl-5-[4-(diphenylmethyl)-1-piperazinylmethyl]-1H-benzimidazol-2-ylmethyl}acetateYield 22.8%

Procedure

A mixture of 12.9 parts of N1 -butyl-4-[4(diphenylmethyl)-1-piperazinylmethyl]-1,2-benzenediamine, 4.6 parts of ethyl 2-hydroxyethanimidate hydrochloride and 100 parts of acetic acid is stirred overnight at room temperature. The whole is heated to reflux and stirring is continued for 3 hours at reflux temperature. The solvent is evaporated in vacuo and the residue is stirred in water. The free base is liberated in the conventional manner with ammonium hydroxide and 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 fractions with the highest Rf-value are collected and the eluent is evaporated. The residue is crystallized from 21 parts of 2,2'-oxybispropane. The product is filtered off, washed with 2,2'-oxybispropane and dried, yielding 3.5 parts (22.8%) of {1-butyl-5-[4-(diphenylmethyl)-1-piperazinylmethyl]-1H-benzimidazol-2-ylmethyl}acetate; mp. 151.2° C.

Workup

  1. temperatureThe whole is heated
  2. temperatureto reflux
  3. stirringstirring
  4. waitis continued for 3 hours
  5. temperatureat reflux temperature
  6. customThe solvent is evaporated in vacuo
  7. stirringthe residue is stirred in water
  8. extractionextracted with trichloromethane
  9. customThe extract is dried
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue is purified by column-chromatography over silica gel using
  13. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  14. customThe fractions with the highest Rf-value are collected
  15. customthe eluent is evaporated
  16. customThe residue is crystallized from 21 parts of 2,2'-oxybispropane
  17. filtrationThe product is filtered off
  18. washwashed with 2,2'-oxybispropane
  19. customdried

Sources & evidence

ORD record
ord-532d44036cf8460cb05e613ded5fd6ad
Source dataset
uspto-grants-1981_01
Patent number
US04243806

Reaction notes

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