Benzene → HCID 21428959, compound

HRID 437631Notes

Reaction equation

HRID 437631 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([N:8]1[CH2:10][CH2:9]1)=[O:7].[NH:11]1[CH2:16][CH2:15][CH:14]([N:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[NH:19][C:18]2=[O:26])[CH2:13][CH2:12]1.C1C=CC=CC=1.CO>ClC(Cl)Cl>[O:26]=[C:18]1[N:17]([CH:14]2[CH2:13][CH2:12][N:11]([CH2:9][CH2:10][NH:8][C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[O:7])[CH2:16][CH2:15]2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[NH:19]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 887MethanolHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 21428881HCID 21428881, compound

Product 1

HCID 21428959HCID 21428959, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 7.7 parts of 1-(2-thienylcarbonyl)aziridine, 10.8 parts of 1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one, 54 parts of benzene and 8 parts of methanol is stirred and refluxed for 1.50 hours. The reaction mixture is cooled and trichloromethane is added. The undissolved product is filtered off and stirred in 2,2'-oxybispropane. It is filtered off again and crystallized twice: first from a mixture of methanol and N,N-dimethylformamide and then from a mixture of trichloromethane and methanol, yielding 4 parts of N-{2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl] ethyl}-2-thiophenecarboxamide; mp. + 300° C (dec.).

Workup

  1. temperaturerefluxed for 1.50 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationThe undissolved product is filtered off
  4. stirringstirred in 2,2'-oxybispropane
  5. filtrationIt is filtered off again
  6. customcrystallized twice
  7. additionfirst from a mixture of methanol and N,N-dimethylformamide
  8. additionfrom a mixture of trichloromethane and methanol

Sources & evidence

ORD record
ord-9c9c1e1593ed4c17bc58ed99ff82c2e7
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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