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

HRID 51261Notes

Reaction equation

HRID 51261 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]>CO.[Rh]>[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

4

Reactant 1

HCID 314742(2,3-Dimethoxyphenyl)(4-pyridinyl)methanol

Product 1

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

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

4-[1-Hydroxy-1-(2,3-dimethoxyphenyl)methyl]pyridine (10) (10.1 g, 41 mmol) was dissolved in 100 mL of methanol and hydrogenated using a 5% rhodium on carbon catalyst. At the conclusion of the reaction, the catalyst was removed by filtration. The filtrate weighed 111.51 g. The reactor and catalyst cake were washed with methanol. The combined washes weighed 170.27 g and contained 7.6% of the title compound (11).

Workup

  1. customAt the conclusion of the reaction
  2. customthe catalyst was removed by filtration
  3. washThe reactor and catalyst cake were washed with methanol

Sources & evidence

ORD record
ord-474ac78b11034081939b9ee0b0af8714
Source dataset
uspto-grants-2004_03
Patent number
US06713627B2

Reaction notes

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