Ethyl orthoformate → HCID 20298824, compound

HRID 1448095Notes

Reaction equation

HRID 1448095 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:16]=[C:17]([NH2:25])[C:18]([NH:21][CH2:22][CH2:23][CH3:24])=[CH:19][CH:20]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:32](OCC)(OCC)OCC>C(O)(=O)C>[C:26]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:9][CH2:10][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]4[N:21]([CH2:22][CH2:23][CH3:24])[CH:32]=[N:25][C:17]=4[CH:16]=3)[CH2:12][CH2:13]2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 53790858HCID 53790858, compound

Product 1

HCID 20298824HCID 20298824, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5 parts of 4-[4-(diphenylmethyl)-1-piperazinylmethyl]-N1 -propyl-1,2-benzenediamine, 35 parts of 1,1',1"-[methylidynetris(oxy)]trisethane and 1.5 parts of acetic acid is stirred and refluxed for 2 hours. The reaction mixture is cooled and evaporated. The residue is taken up in 100 parts of water and a hydrochloric acid solution 10 N is added till all solid enters solution. This solution is treated with activated charcoal. The latter is filtered off and the filtrate is alkalized with a sodium hydroxide solution. 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 (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 4-methyl-2-pentanone. The product is filtered off, washed with a small amount of 4-methyl-2-pentanone and with 2,2'-oxybispropane, and dried, yielding 2.2 parts of 5-[4-(diphenylmethyl)- 1-piperazinylmethyl]-1-propyl-1H-benzimidazole; mp. 154.8° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureThe reaction mixture is cooled
  3. customevaporated
  4. additiona hydrochloric acid solution 10 N is added till all solid
  5. additionThis solution is treated with activated charcoal
  6. filtrationThe latter is filtered off
  7. extractionThe product is extracted with dichloromethane
  8. customThe extract is dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue is purified by column-chromatography over silica gel using
  12. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  13. customThe pure fractions are collected
  14. customthe eluent is evaporated
  15. customThe residue is crystallized from 4-methyl-2-pentanone
  16. filtrationThe product is filtered off
  17. washwashed with a small amount of 4-methyl-2-pentanone and with 2,2'-oxybispropane
  18. customdried

Sources & evidence

ORD record
ord-103abe9031c04f98b585f1c2fe6aa816
Source dataset
uspto-grants-1979_12
Patent number
US04179505

Reaction notes

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