Trimethyl orthoformate → HCID 20298702, compound

HRID 1448103Notes

Reaction equation

HRID 1448103 reaction equation
[C:1]1([CH:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:16]=[C:17]([NH2:26])[C:18]([NH:21][CH2:22][CH2:23][O:24][CH3:25])=[CH:19][CH:20]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:33]OC(OC)OC>C(O)(=O)C>[C:27]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]4[N:21]([CH2:22][CH2:23][O:24][CH3:25])[CH:33]=[N:26][C:17]=4[CH:16]=3)[CH2:10][CH2:9]2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 9005Trimethyl orthoformateHCID 53838096HCID 53838096, compound

Product 1

HCID 20298702HCID 20298702, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2.8 parts of 4-[4-(diphenylmethyl)-1-piperazinylmethyl]-N1 -(2-methoxyethyl)-1,2-benzenediamine, 20 parts of trimethoxymethane and 0.39 parts of acetic acid is stirred and refluxed for 1.50 hours. The reaction mixture is evaporated and the residue is dissolved in a diluted hydrochloric acid solution. The free base is liberated in the conventional manner with ammonium hydroxide and extracted with dichloromethane. The extract is dried, filtered and evaporated. The residue is washed with 2,2'-oxybispropane and dried, yielding 2 parts (70%) of 5-[4-(diphenylmethyl)-1-piperazinylmethyl]-1-(2-methoxyethyl)-1H-benzimidazole; mp. 161.7° C.

Workup

  1. temperaturerefluxed for 1.50 hours
  2. customThe reaction mixture is evaporated
  3. dissolutionthe residue is dissolved in a diluted hydrochloric acid solution
  4. extractionextracted with dichloromethane
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated
  8. washThe residue is washed with 2,2'-oxybispropane
  9. customdried

Sources & evidence

ORD record
ord-983540b35f8042819386e29d5117b198
Source dataset
uspto-grants-1979_12
Patent number
US04179505

Reaction notes

Loading…