Toluene → HCID 13105519, compound

HRID 2050282Notes

Reaction equation

HRID 2050282 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:15][CH2:16][N:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[NH:19][C:18]1=[O:26].CC1C=CC=CC=1>O>[C:1]1([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([CH2:15][CH2:16][N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[NH:19][C:18]3=[O:26])[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 759941-BenzylpiperazineHCID 36534711-(2-Chloroethyl)-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 13105519HCID 13105519, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 70.4 parts of 1-(phenylmethyl)piperazine, 39.4 parts of 1-(2-chloroethyl)-1,3-dihydro-2H-benzimidazol-2-one and 360 parts of methylbenzene is stirred and refluxed overnight. The reaction mixture is cooled, water is added and the layers are separated. The methylbenzene-phase is washed three times with water, dried, filtered and evaporated. The solid residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is boiled in 2,2'-oxybispropane. The whole is cooled on an ice-bath. The product is filtered off and crystallized from a mixture of 2,2'-oxybispropane and a small amount of 2-propanol, yielding 1,3-dihydro-1-{2-[4-(phenylmethyl)-1-piperazinyl]ethyl}-2H-benzimidazol-2-one; mp. 136.5° C.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture is cooled
  3. customthe layers are separated
  4. washThe methylbenzene-phase is washed three times with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe solid residue is purified by column-chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (95:5) as eluent
  10. customThe pure fractions are collected
  11. customthe eluent is evaporated
  12. temperatureThe whole is cooled on an ice-bath
  13. filtrationThe product is filtered off
  14. customcrystallized from a mixture of 2,2'-oxybispropane

Sources & evidence

ORD record
ord-2cbdda145e174f5cbd1211c67f00a942
Source dataset
uspto-grants-1980_04
Patent number
US04200641

Reaction notes

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