Toluene → 1-acetyl-3-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1,3-dihydro-2H-benzimidazol-2-one

HRID 354997

Reaction equation

HRID 354997 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[C:8]1([CH:14]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][N:24]3[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[NH:26][C:25]3=[O:33])[CH2:17][CH2:16]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC1C=CC=CC=1>O>[C:5]([N:26]1[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[N:24]([CH2:23][CH2:22][CH2:21][N:18]2[CH2:19][CH2:20][N:15]([CH:14]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:16][CH2:17]2)[C:25]1=[O:33])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 1140TolueneHCID 4615OxatomideHCID 7918Acetic Anhydride

Product 1

HCID 131055881-acetyl-3-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1,3-dihydro-2H-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.55 parts of acetic acid anhydride, 3 parts of 1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1,3-dihydro-2H-benzimidazol-2-one and 22.5 parts of methylbenzene is stirred and refluxed overnight. Water is added to the reaction mixture and the layers are separated. 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, yielding 1-acetyl-3-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1,3-dihydro-2H-benzimidazol-2-one; mp. 124.4° C.

Workup

  1. temperaturerefluxed overnight
  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

Sources & evidence

ORD record
ord-aad8a92e033a43599bf0eefee954b6b3
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Linked notes

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