Hydrochloric Acid → alpha-(4-Methoxyphenyl)-1-(2-phenylethyl)-4-piperidinemethanol hydrochloride

HRID 1165863Notes

Reaction equation

HRID 1165863 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:5]=1.C[O-].[Na+].[BH4-].[Na+].Cl>CCO.CO.CCOC(C)=O>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:17]2)[OH:11])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 14257843(4-Methoxyphenyl)[1-(2-phenylethyl)-4-piperidinyl]-methanone hydrochloride

Product 1

HCID 14257857alpha-(4-Methoxyphenyl)-1-(2-phenylethyl)-4-piperidinemethanol hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of (4-methoxyphenyl)[1-(2-phenylethyl)-4-piperidinyl]-methanone hydrochloride (3.5 g, 9.7 mmol) in absolute EtOH (75 ml) was treated with sodium methoxide (0.53 g, 9.7 mmol) followed by sodium borohydride (1.08 g, 20 mmol) and the mixture stirred for 42 h at room temperature. The reaction mixture was filtered and the filtrate concentrated to a solid residue which was dissolved in absolute Et2O and treated with HCl (9.7 mmol) dissolved in CH3OH/EtOAc (1:3, 8 ml). The resulting precipitate was filtered and recrystallized from CH3OH/Et2O to give alpha-(4-methoxyphenyl)-1-(2-phenylethyl)-4-piperidinemethanol hydrochloride, mp 162.5°-164° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated to a solid residue which
  3. dissolutionwas dissolved in absolute Et2O
  4. filtrationThe resulting precipitate was filtered
  5. customrecrystallized from CH3OH/Et2O

Sources & evidence

ORD record
ord-36d96d5c54fc4be8ba9d3444ea996f6c
Source dataset
uspto-grants-1990_03
Patent number
US04912117

Reaction notes

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