(2,3-Dimethoxyphenyl)(piperidin-4-yl)methanol → (R)-(2,3-Dimethoxyphenyl)-4-piperidinemethanol

HRID 51267Notes

Reaction equation

HRID 51267 reaction equation
[OH:1][CH:2]([CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[O:11][CH3:12]>C(O)(C)C>[CH3:12][O:11][C:4]1[C:5]([O:9][CH3:10])=[CH:6][CH:7]=[CH:8][C:3]=1[C@@H:2]([CH:13]1[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]1)[OH:1]

Participants

3

Reactant 1

HCID 10890362(2,3-Dimethoxyphenyl)(piperidin-4-yl)methanol

Product 1

HCID 9859798(R)-(2,3-Dimethoxyphenyl)-4-piperidinemethanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Dissolve 4-[1-hydroxy-1-(2,3-dimethoxyphenyl)methyl]piperidine (11) (11.0 g, 43.8 mmol) and 17.0 g (40.1 mmol) (2R,3R)-(−)-di-(p-anisoyl)tartaric acid in 400 mL refluxing isopropanol. Allow the mixture to cool to room temperature. Collect the precipitate, rinse with isopropanol and dry to give the (R)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol, (2R,3R)-(−)-di-(p-anisoyl)tartaric acid. Recrystallize the (R)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol, (2R,3R)-(−)-di-(p-anisoyl)tartaric acid salt from 250 mL isopropanol.

Workup

  1. customCollect the precipitate
  2. washrinse with isopropanol
  3. customdry

Sources & evidence

ORD record
ord-48ccfe1622554e269225f63a68a2b893
Source dataset
uspto-grants-2004_03
Patent number
US06713627B2

Reaction notes

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