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

HRID 1681085Notes

Reaction equation

HRID 1681085 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-5279af027eb64ee192bbe0c8ec440244
Source dataset
uspto-grants-1992_12
Patent number
US05169096

Reaction notes

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