Hydrochloric Acid → HCID 20298760, compound

HRID 1389317Notes

Reaction equation

HRID 1389317 reaction equation
[C:1]1([CH:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:16]=[C:17]([NH2:23])[C:18]([NH:21][CH3:22])=[CH:19][CH:20]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:30][C:31]1[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=1.[N+](C1C=CC=CC=1)([O-])=O.Cl>O>[Cl:30][C:31]1[CH:38]=[CH:37][C:34]([C:35]2[N:21]([CH3:22])[C:18]3[CH:19]=[CH:20][C:15]([CH2:14][N:11]4[CH2:12][CH2:13][N:8]([CH:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)[C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:9][CH2:10]4)=[CH:16][C:17]=3[N:23]=2)=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7416NitrobenzeneHCID 77264-ChlorobenzaldehydeHCID 30178794-{[4-(Diphenylmethyl)piperazin-1-yl]methyl}-N~1~-methylbenzene-1,2-diamine

Product 1

HCID 20298760HCID 20298760, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3.9 parts of 4-[4-(diphenylmethyl)-1-piperazinylmethyl]-N1 -methyl-1,2-benzenediamine, 2.5 parts of 4-chlorobenzaldehyde and 18 parts of nitrobenzene is stirred in an oil-bath first for 1 hour at 50° C. and further for 1.50 hours at 120° C. The reaction mixture is cooled and allowed to stand overnight at room temperature. About 100 parts of water are added and the whole is acidified with a hydrochloric acid solution 10 N. The product is extracted with 2,2'-oxybispropane. The aqueous phase is treated with activated charcoal. The latter is filtered off and the filtrate is alkalized with a sodium hydroxide solution 50%. The product is extracted with dichloromethane. The extract is washed with water, dried, filtered and evaporated. The residue is crystallized from 35 parts of 1,1'-oxybisethane. The product is filtered off, washed with 1,1'-oxybisethane and dried, yielding 1.3 parts of 2-(4-chlorophenyl)-5-[4-(diphenylmethyl)-1-piperazinylmethyl]- 1-methyl-1H-benzimidazole; mp. 198.3° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. waitto stand overnight at room temperature
  3. extractionThe product is extracted with 2,2'-oxybispropane
  4. additionThe aqueous phase is treated with activated charcoal
  5. filtrationThe latter is filtered off
  6. extractionThe product is extracted with dichloromethane
  7. washThe extract is washed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue is crystallized from 35 parts of 1,1'-oxybisethane
  12. filtrationThe product is filtered off
  13. washwashed with 1,1'-oxybisethane
  14. customdried

Sources & evidence

ORD record
ord-c8c22065f4574cb486ca7ef6052e285e
Source dataset
uspto-grants-1981_01
Patent number
US04243806

Reaction notes

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