Sodium Hydroxide → HCID 178519937, compound

HRID 1448107Notes

Reaction equation

HRID 1448107 reaction equation
[C:1]1([CH:7]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:33]=[CH:32][C:18]4[NH:19][C:20]([CH2:22][O:23]C(=O)C5C=CC=CC=5)=[N:21][C:17]=4[CH:16]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:34]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:33]=[CH:32][C:18]4[NH:19][C:20]([CH2:22][OH:23])=[N:21][C:17]=4[CH:16]=3)[CH2:10][CH2:9]2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178525237HCID 178525237, compound

Product 1

HCID 178519937HCID 178519937, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of 8.8 parts of {5-[4-(diphenylmethyl)-1-piperazinylmethyl]-1H-benzimidazol-2-ylmethyl}benzoate and 120 parts of methanol are added 13.5 parts of sodium hydroxide solution 50% and the whole is stirred and refluxed for 30 minutes. The reaction mixture is evaporated and the residue is stirred in water. The product is extracted with dichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 45 parts of methylbenzene. The product is filtered off, washed with 2,2'-oxybispropane and dried, yielding 4 parts (57%) of 5-[4-(diphenylmethyl)-1-piperazinylmethyl]-1H-benzimidazole-2-methanol; mp. 137.1° C.

Workup

  1. temperaturerefluxed for 30 minutes
  2. customThe reaction mixture is evaporated
  3. stirringthe residue is stirred in water
  4. extractionThe product is extracted with dichloromethane
  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 (90:10 by volume) as eluent
  10. customThe pure fractions are collected
  11. customthe eluent is evaporated
  12. customThe residue is crystallized from 45 parts of methylbenzene
  13. filtrationThe product is filtered off
  14. washwashed with 2,2'-oxybispropane
  15. customdried

Sources & evidence

ORD record
ord-fd49ac81ff3d43b58ad6d0e3deb96ea0
Source dataset
uspto-grants-1979_12
Patent number
US04179505

Reaction notes

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