Hydrochloric Acid → HCID 11426865, compound

HRID 1681082Notes

Reaction equation

HRID 1681082 reaction equation
Cl.[C:2]1([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:12][CH2:11]2)=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[BH4-].[Na+].Cl.[OH-].[Na+]>C(O)C.CO.CCOC(C)=O.O>[C:2]1([CH:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:12][CH2:11]2)[OH:9])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 14257849HCID 14257849, compound

Product 1

HCID 11426865HCID 11426865, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

To a stirred solution of phenyl[1-(3-phenylpropyl)-4-piperidinyl]-methanone hydrochloride (6.8 g, 0.02 mol) in absolute ethanol (120 ml) was added sodium methoxide (1.08 g, 0.04 mol) followed by sodium borohydride (1.51 g, 0.04 mol). The reaction mixture was stirred for 72 h and then concentrated at reduced pressure to a solid residue. This material was stirred with aqueous 10% NaOH for 1 h and then extracted with toluene (2×50 ml). The extracts were washed with water and then saturated NaCl solution. The toluene solution was dried over MgSO4, filtered and concentrated to a colorless oil. This material was dissolved in dry Et2O (50 ml) and treated with a solution of HCl (0.02 mol) in CH3OH/EtOAc (1:4, 12.5 ml). The resultant precipitate was dissolved in water, basified using 10% aqueous NaOH and extracted into toluene. The toluene solution was washed with saturated aqueous NaCl dried over MgSO4, filtered and concentrated to a solid. This material was flash chromatographed on a 2.5×6.0 inch silica gel column, and eluted with CH3OH/CH2Cl2 (1:9). The resultant fractions (7-9) eventually solidified and were recrystallized from acetone to give alpha-phenyl-1-(3-phenylpropyl)-4-piperidinemethanol, mp 87°-88° C.

Workup

  1. concentrationconcentrated at reduced pressure to a solid residue
  2. stirringThis material was stirred with aqueous 10% NaOH for 1 h
  3. extractionextracted with toluene (2×50 ml)
  4. washThe extracts were washed with water
  5. dry with materialThe toluene solution was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to a colorless oil
  8. dissolutionThis material was dissolved in dry Et2O (50 ml)
  9. extractionextracted into toluene
  10. washThe toluene solution was washed with saturated aqueous NaCl
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated to a solid
  14. customchromatographed on a 2.5×6.0 inch silica gel column
  15. washeluted with CH3OH/CH2Cl2 (1:9)
  16. customwere recrystallized from acetone

Sources & evidence

ORD record
ord-6b46ca06d637422d9fb234aa0ac64c8f
Source dataset
uspto-grants-1992_12
Patent number
US05169096

Reaction notes

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