Sodium Carbonate → HCID 21428928, compound

HRID 437669Notes

Reaction equation

HRID 437669 reaction equation
[ClH:1].[Cl:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:7].[NH:14]1[CH2:19][CH2:18][CH:17]([N:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[NH:22][C:21]2=[O:29])[CH2:16][CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)CC(=O)C>[OH2:7].[ClH:2].[ClH:1].[O:29]=[C:21]1[N:20]([CH:17]2[CH2:16][CH2:15][N:14]([CH2:3][CH2:4][NH:5][C:6]([C:8]3[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=3)=[O:7])[CH2:19][CH2:18]2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[NH:22]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 21428916HCID 21428916, compound

Product 1

HCID 21428928HCID 21428928, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 8.8 parts of N-(2-chloroethyl)-3-pyridinecarboxamide hydrochloride, 4.6 parts of 1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one, 4.24 parts of sodium carbonate and 120 parts of 4-methyl-2-pentanone is stirred and refluxed for 48 hours. The reaction mixture is cooled to room temperature and poured onto water. The product is extracted five times with trichloromethane. The combined extracts are 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 converted into the hydrochloride salt in ethanol and 2-propanol. The salt is filtered off and crystallized from a mixture of methanol and ethanol. It is filtered off again and recrystallized from a mixture of ethanol and 2,2'-oxybispropane, yielding 0.8 parts of N-{2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl}-3-pyridinecarboxamide dihydrochloride hydrate; mp. 214.1° C.

Workup

  1. temperaturerefluxed for 48 hours
  2. additionpoured onto water
  3. extractionThe product is extracted five times with trichloromethane
  4. customThe combined extracts are dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. filtrationThe salt is filtered off
  12. customcrystallized from a mixture of methanol and ethanol
  13. filtrationIt is filtered off again
  14. customrecrystallized from a mixture of ethanol and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-45f18c93df55478fb92f3b37da3ee12a
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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