Hydrochloric Acid → HCID 23285014, compound

HRID 369194Notes

Reaction equation

HRID 369194 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 resiude 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 5 N hydrochloric acid, in ethanol. The hydrochloride was crystallized from ethyl acetateethanol 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 resiude was purified by a silica gel column chromatography (eluant: dichloromethane/methanol=45/1 to 25/1)
  13. customThe hydrochloride was crystallized from ethyl acetateethanol
  14. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-2cbe2327e2674b5aa103f6e5b49d9769
Source dataset
uspto-grants-2000_10
Patent number
US06136826

Reaction notes

Loading…