Hydrochloric Acid → HCID 23285014, compound

HRID 962792Notes

Reaction equation

HRID 962792 reaction equation
CO.[CH3:3][N:4]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]([C:21]2[CH:22]=[CH:23][C:24]([C:27](OC)=[O:28])=[N:25][CH:26]=2)=[O:20])[CH2:15][CH2:14]1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[BH4-].[Na+].[ClH:33]>C(O)C.C(O)(=O)C.O.C(O)(C)(C)C>[ClH:33].[ClH:33].[CH3:3][N:4]([CH:13]1[CH2:14][CH2:15][N:16]([C:19]([C:21]2[CH:22]=[CH:23][C:24]([CH2:27][OH:28])=[N:25][CH:26]=2)=[O:20])[CH2:17][CH2:18]1)[CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

9

Reactant 4

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

Product 1

HCID 23285014HCID 23285014, 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 silica 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 silica 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-011f5aa9b4424c36ba07bcb71d5bc2c2
Source dataset
uspto-grants-1998_06
Patent number
US05760058

Reaction notes

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