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

HRID 2055862Notes

Reaction equation

HRID 2055862 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-30c518fc4dc241d7bbdfbb5389c87b17
Source dataset
uspto-grants-2008_02
Patent number
US07332607B2

Reaction notes

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