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

HRID 2055863Notes

Reaction equation

HRID 2055863 reaction equation
[OH:1][CH:2]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[O:11][CH3:12].[H][H]>[Rh].CO>[OH:1][CH:2]([CH:13]1[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]1)[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[O:11][CH3:12]

Participants

5

Reactant 2

HCID 314742(2,3-Dimethoxyphenyl)(4-pyridinyl)methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 10890362(2,3-Dimethoxyphenyl)(piperidin-4-yl)methanolYield 90%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A 1-L Parr reactor was charged with 12.43 g (0.051 mol) of 4-[1-hydroxy-1-(2,3-dimethoxyphenyl)methyl]pyridine (10), 5.74 g of a 5% Rhodium on Carbon catalyst, and 237 g of methanol. The solution was warmed to 40° C. and treated with 100 psi of hydrogen for 5.5 h. When the reaction was complete, the solution was filtered and the catalyst washed with 108 g of methanol which was added to the filtrate. The weight of the filtered solution was 310.45 g. The methanol solution was assayed for the title compound using high pressure liquid chromatography. The methanol solution was found to contain 3.7% title compound by weight. This corresponds to 11.5 g (90% yield) of title compound.

Workup

  1. filtrationthe solution was filtered
  2. washthe catalyst washed with 108 g of methanol which
  3. additionwas added to the filtrate

Sources & evidence

ORD record
ord-f5ce8d5cdadf499b8c4a0667fea556e6
Source dataset
uspto-grants-2008_02
Patent number
US07332607B2

Reaction notes

Loading…