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

HRID 1413522
Notes
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Reaction equation

HRID 1413522 reaction equation
N[C:2](N)=[O:3].[C:5]1([CH:11]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][NH:21][C:22]3[C:23]([NH2:32])=[CH:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=3)[CH2:14][CH2:13]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.ClC(Cl)Cl>O>[C:33]1([CH:11]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][N:21]3[C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:24][C:23]=4[NH:32][C:2]3=[O:3])[CH2:14][CH2:13]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1176UreaHCID 6212ChloroformHCID 86736963N1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-4-(trifluoromethyl)-1,2-benzenediamine

Product 1

HCID 131055811-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1,3-dihydro-5-(trifluoromethyl)-2H-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 5.4 parts of urea and 13.7 parts of N1 -{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-4-(trifluoromethyl)-1,2-benzenediamine is stirred and heated for 4 hours at 190° C. The reaction mixture is cooled to room temperature and diluted with water. After the addition of trichloromethane, the layers are separated. The aqueous phase is extracted with trichloromethane. The combined organic phases are washed with water, dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 2,2'-oxybispropane. The product is filtered off and dried, yielding 1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1,3-dihydro-5-(trifluoromethyl)-2H-benzimidazol-2-one; mp. 152.7° C.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customthe layers are separated
  3. extractionThe aqueous phase is extracted with trichloromethane
  4. washThe combined organic phases are washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe oily residue is purified by column-chromatography over silica gel
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. customThe residue is crystallized from 2,2'-oxybispropane
  12. filtrationThe product is filtered off
  13. customdried

Sources & evidence

ORD record
ord-6a478b50cff14f40bc5ad50f960f5772
Source dataset
uspto-grants-1981_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04250176

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes