Water → 5,6-dichloro-1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1,3-dihydro-2H-benzimidazol-2-one

HRID 2050314Notes

Reaction equation

HRID 2050314 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:32])[C:5]([NH: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)=[CH:6][C:7]=1[Cl:8].N[C:34](N)=[O:35].O>ClC(Cl)Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[N:9]([CH2:10][CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][N:16]([CH:19]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:17][CH2:18]3)[C:34](=[O:35])[NH:32][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1176UreaHCID 537535764,5-dichloro-N1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1,2-benzenediamine

Product 1

HCID 131055825,6-dichloro-1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1,3-dihydro-2H-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 4 parts of 4,5-dichloro-N1 -{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1,2-benzenediamine and 1.5 parts of urea is stirred for 3 hours in an oil-bath at 190° C. After cooling, water and trichloromethane are added. The layers are separated and the organic phase 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 methylbenzene and 2,2'-oxybispropane, yielding 5,6-dichloro-1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1,3-dihydro-2H-benzimidazol-2-one; mp. 214.3° C.

Workup

  1. temperatureAfter cooling
  2. customThe layers are separated
  3. customthe organic phase is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by column-chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated
  10. customThe residue is crystallized from a mixture of methylbenzene and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-c21743e2cdb94dbbaf755d1f4f820877
Source dataset
uspto-grants-1980_04
Patent number
US04200641

Reaction notes

Loading…