Hydrochloric Acid → HCID 131720111, compound

HRID 2257154Notes

Reaction equation

HRID 2257154 reaction equation
CO.CN(C1CCN(C([C:21]2[CH:22]=[CH:23][C:24]([C:27](OC)=[O:28])=[N:25][CH:26]=2)=O)CC1)CCC1C=CC=CC=1.[BH4-].[Na+].[ClH:33]>C(O)C.C(O)(=O)C.O.C(O)(C)(C)C>[ClH:33].[ClH:33].[C:27](=[C:24]1[CH2:23][CH2:22][CH2:21][CH2:26][NH:25]1)=[O:28]

Participants

9

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 4311764Sodium borohydrideHCID 23284959HCID 23284959, compound

Product 1

HCID 131720111HCID 131720111, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

1 ml of methanol was dropwise added, at about 80° C. to a mixture of 1.0 g of 4-[N-methyl-N-(2-phenylethyl)amino]-1(2-methoxycarbonylpyridin-5-yl)carbonylpiperidine, 0.12 g of sodium borohydride and 3.88 g of tert-butanol. (This gave rise to foaming.) In this state, the mixture was refluxed by heating, for 1.5 hours. The reaction mixture was returned to room temperature and mixed with 1 ml of water and 1 ml of acetic acid. The mixture was stirred for 5 minutes and then subjected to distillation to remove the solvent. The residue was mixed with water for dissolution. The solution was made basic with an aqueous sodium hydroxide solution and then extracted with chloroform. The extract was washed with water and a saturated aqueous sodium chloride solution, dried with magnesium sulfate, and subjected to distillation to remove the solvent. The residue was purified by a silical gel column chromatography (eluant:dichloromethane/methanol=45/1 to 25/1). The product was converted to a hydrochloride with 2 equivalents of 5N hydrochloric acid, in ethanol. The hydrochloride was crystallized from ethyl acetate-ethanol and recrystallized from ethanol-water to obtain 0.32 g of 4-[N-methyl-N-(2-phenylethyl)amino]-1-2-hydroxymethylpyridin-5-yl)carbonylpiperidine dihydrochloride as colorless prism-like crystals.

Workup

  1. temperature) In this state, the mixture was refluxed
  2. temperatureby heating, for 1.5 hours
  3. customwas returned to room temperature
  4. distillationsubjected to distillation
  5. customto remove the solvent
  6. additionThe residue was mixed with water for dissolution
  7. extractionextracted with chloroform
  8. washThe extract was washed with water
  9. dry with materiala saturated aqueous sodium chloride solution, dried with magnesium sulfate
  10. distillationsubjected to distillation
  11. customto remove the solvent
  12. customThe residue was purified by a silical gel column chromatography (eluant:dichloromethane/methanol=45/1 to 25/1)
  13. customThe hydrochloride was crystallized from ethyl acetate-ethanol
  14. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-edd368c308164d77aef8398a45e563fd
Source dataset
uspto-grants-1997_08
Patent number
US05656642

Reaction notes

Loading…