Ethyl chloroformate → HCID 14012878, compound

HRID 1904831Notes

Reaction equation

HRID 1904831 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:16][CH:17]2[CH2:22][CH2:21][N:20](CC3C=CC=CC=3)[CH2:19][CH2:18]2)=[CH:2]1.C(Cl)(=O)OCC>CC1C=CC=CC=1>[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:16][CH:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2)=[CH:2]1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 14012852HCID 14012852, compound

Product 1

HCID 14012878HCID 14012878, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred mixture of 72 parts of 1-(3-furanylmethyl)-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-benzimidazole and 324 parts of methylbenzene were added dropwise 25.5 parts of ethyl carbonochloridate at reflux. Upon completion, stirring was continued for 2 hours at reflux temperature. After cooling, the mixture was washed twice with a sodium hydroxide solution 5%, once with water, dried, filtered and evaporated. This residue, together with 560 parts of 2-propanol, 69.9 parts of potassium hydroxide and 6 parts of water, was stirred and refluxed for 22 hours. The whole was cooled and evaporated. The residue was taken up in water. The product was extracted three times with dichloromethane. The combined extracts were washed twice with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane, methanol and ammonium hydroxide (90:10:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was stirred in 2-propanone. The product was filtered off and dried, yielding 28.0 parts (49.8%) of 1-(3-furanylmethyl)-2-(4-piperidinylmethyl)-1H-benzimidazole; mp. 180° C. (73).

Workup

  1. temperatureat reflux
  2. temperatureat reflux temperature
  3. temperatureAfter cooling
  4. washthe mixture was washed twice with a sodium hydroxide solution 5%, once with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. stirringThis residue, together with 560 parts of 2-propanol, 69.9 parts of potassium hydroxide and 6 parts of water, was stirred
  9. temperaturerefluxed for 22 hours
  10. temperatureThe whole was cooled
  11. customevaporated
  12. extractionThe product was extracted three times with dichloromethane
  13. washThe combined extracts were washed twice with water
  14. customdried
  15. filtrationfiltered
  16. customevaporated
  17. customThe residue was purified by column chromatography over silica gel using
  18. additiona mixture of trichloromethane, methanol and ammonium hydroxide (90:10:1 by volume) as eluent
  19. customThe pure fractions were collected
  20. customthe eluent was evaporated
  21. stirringThe residue was stirred in 2-propanone
  22. filtrationThe product was filtered off
  23. customdried

Sources & evidence

ORD record
ord-c9111bb7bf3c48f9895b05f0eb3b1313
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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