N,N-Dimethylaniline → HCID 20298796, compound

HRID 1389310Notes

Reaction equation

HRID 1389310 reaction equation
[C:1]1([CH:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:25]=[CH:24][C:18]4[N:19]([CH2:22][CH3:23])[CH:20]=[N:21][C:17]=4[CH:16]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2-].[Na+].C[N:35](C)C1C=CC=CC=1>>[C:26]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:25]=[CH:24][C:18]4[N:19]([CH2:22][CH3:23])[C:20]([NH2:35])=[N:21][C:17]=4[CH:16]=3)[CH2:10][CH2:9]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24533Sodium amideHCID 20298827HCID 20298827, compound

Product 1

HCID 20298796HCID 20298796, compound

Conditions

Temperature
135 °C

Procedure

A mixture of 4.1 parts of 5-[4-(diphenylmethyl)-1-piperazinylmethyl]-1-ethyl-1H-benzimidazole, 1.2 parts of sodium amide and 20 parts of N,N-dimethylbenzenamine is stirred and heated slowly to 135° C. Stirring at 135° C. is continued for 3 hours. The reaction mixture is cooled and poured onto water. The product is extracted with trichloromethane. The extract 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) and a small amount of ammonium hydroxide as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from methylbenzene. The product is filtered off and dried, yielding 1.5 parts of 5-[4-(diphenylmethyl)-1-piperazinylmethyl]-1-ethyl-1H-benzimidazol-2-amine; mp. 214.3° C.

Workup

  1. stirringStirring at 135° C.
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water
  4. extractionThe product is extracted with trichloromethane
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by column-chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (95:5 by volume)
  10. customThe pure fractions are collected
  11. customthe eluent is evaporated
  12. customThe residue is crystallized from methylbenzene
  13. filtrationThe product is filtered off
  14. customdried

Sources & evidence

ORD record
ord-58467af5afc24060b43c234e15911e00
Source dataset
uspto-grants-1981_01
Patent number
US04243806

Reaction notes

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