Hydrochloric Acid → 1-{3-[4-(diphenylmethyl)piperazinyl]propyl}-1H-benzimidazol-2-amine

HRID 2050317Notes

Reaction equation

HRID 2050317 reaction equation
COC(=O)[NH:4][C:5]1[N:9]([CH2:10][CH2:11][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)[C:8]2[CH:32]=[CH:33][CH:34]=[CH:35][C:7]=2[N:6]=1.Cl>C(O)C>[C:26]1([CH:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:16]2[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][CH2:10][N:9]3[C:8]4[CH:32]=[CH:33][CH:34]=[CH:35][C:7]=4[N:6]=[C:5]3[NH2:4])[CH2:14][CH2:15]2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13105584methyl [1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1H-benzimidazol-2-yl]carbamate

Product 1

HCID 131055851-{3-[4-(diphenylmethyl)piperazinyl]propyl}-1H-benzimidazol-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 12 parts of methyl[1-{3-[4-(diphenylmethyl)-1-piperazinyl]-propyl}-1H-benzimidazol-2-yl]carbamate, 60 parts of a concentrated hydrochloric acid solution and 80 parts of ethanol is stirred and refluxed overnight. The reaction mixture is evaporated and water is added to the residue. 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 crystallized from ethanol. The product is filtered off and dried, yielding 1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1H-benzimidazol-2-amine; mp. 228.7° C.

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture is evaporated
  3. additionwater is added to the residue
  4. extractionextracted with trichloromethane
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from ethanol
  9. filtrationThe product is filtered off
  10. customdried

Sources & evidence

ORD record
ord-6aada3fcf4964279a95b7baf93827ba0
Source dataset
uspto-grants-1980_04
Patent number
US04200641

Reaction notes

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