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

HRID 51262Notes

Reaction equation

HRID 51262 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-ce3bacdc51c043e1bb44ad49b17a2372
Source dataset
uspto-grants-2004_03
Patent number
US06713627B2

Reaction notes

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