Ethyl chloroformate → HCID 14518011, compound

HRID 1904828Notes

Reaction equation

HRID 1904828 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][C:15]3[N:19]([CH2:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[C:18]4[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=4[N:16]=3)[CH2:10][CH2:9]2)C=CC=CC=1.[C:31](Cl)(=[O:35])[O:32][CH2:33][CH3:34]>CC1C=CC=CC=1>[N:23]1[CH:24]=[CH:25][CH:26]=[C:21]([CH2:20][N:19]2[C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=3[N:16]=[C:15]2[CH2:14][CH:11]2[CH2:12][CH2:13][N:8]([C:31]([O:32][CH2:33][CH3:34])=[O:35])[CH2:9][CH2:10]2)[CH:22]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformate2×HCID 14012848HCID 14012848, compound

Product 1

HCID 14518011HCID 14518011, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred mixture of 76 parts of 2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1-(3-pyridinylmethyl)-1H-benzimidazole and 360 parts of methylbenzene were added dropwise 41 parts of ethyl carbonochloridate. Upon completion, stirring was continued for 2 hours at reflux. Another portion of 5 parts of ethyl carbonochloridate was added dropwise. Upon completion, stirring was continued for 2 hours at reflux. After cooling, the organic layer was washed with a sodium carbonate solution, dried, filtered and evaporated. The residue was purified by filtration over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 35.6 parts (50%) of ethyl 4-[[1-(3-pyridinylmethyl)-1H-benzimidazol-2-yl]methyl]-1-piperidinecarboxylate (57).

Workup

  1. temperatureat reflux
  2. stirringUpon completion, stirring
  3. waitwas continued for 2 hours
  4. temperatureat reflux
  5. temperatureAfter cooling
  6. washthe organic layer was washed with a sodium carbonate solution
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. filtrationThe residue was purified by filtration over silica gel using
  11. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  12. customThe pure fractions were collected
  13. customthe eluent was evaporated

Sources & evidence

ORD record
ord-349cc91c2eca4b309af6c10c2628b073
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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