Sodium Bicarbonate → HCID 86743149, compound

HRID 1904837Notes

Reaction equation

HRID 1904837 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]1=[O:14].[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH2:20][N:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[C:22]1[CH2:30][CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.[C:37](=O)([O-:39])[OH:38].[Na+]>C(O)C>[C:6]([OH:14])(=[O:15])[C:37]([OH:39])=[O:38].[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH2:20][N:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[C:22]1[CH2:30][CH:31]1[CH2:32][CH2:33][N:34]([CH2:2][CH2:3][CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[NH:7][C:6]2=[O:14])[CH2:35][CH2:36]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 18104191-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-oneHCID 14012875HCID 14012875, compound

Product 1

HCID 86743149HCID 86743149, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.16 parts of 1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one, 4.4 parts of 1-(2-furanylmethyl)-2-(4-piperidinylmethyl)-1H-benzimidazole, 2 parts of sodium hydrogen carbonate and 80 parts of ethanol was stirred and refluxed for 32 hours. The reaction mixture was cooled and filtered over Hyflo. The filtrate was evaporated. The residue was purified by column chromatography 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. The residue was converted into the ethanedioate salt in methanol. The salt was filtered off and dried, yielding 4.2 parts (43%) of 1-[3-[4-[[1-(2-furanylmethyl)-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]propyl]-1,3-dihydro-2H-benzimidazol-2-one ethanedioate (1:2); mp. 214.7°-218.4° C. (139).

Workup

  1. temperaturerefluxed for 32 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered over Hyflo
  4. customThe filtrate was evaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. filtrationThe salt was filtered off
  10. customdried

Sources & evidence

ORD record
ord-4460d2d5c6314267809a30ceada9cc65
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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