alpha,alpha-Bis(3-methoxyphenyl)-4-pyridineethanol → alpha,alpha-Bis(3-methoxyphenyl)-4-piperidineethanol

HRID 1249585Notes

Reaction equation

HRID 1249585 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=2)([OH:17])[CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1.[H][H]>C(O)(=O)C.[Pt]=O>[CH3:25][O:24][C:20]1[CH:19]=[C:18]([C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)([OH:17])[CH2:10][CH:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 20223436alpha,alpha-Bis(3-methoxyphenyl)-4-pyridineethanolHCID 178418361HCID 178418361, compound

Product 1

HCID 13754499alpha,alpha-Bis(3-methoxyphenyl)-4-piperidineethanol

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A solution of alpha,alpha-bis(3-methoxyphenyl)-4-pyridine-ethanol (63 g) in acetic acid (400 ml) was hydrogenated over platinum oxide (2 g; 100 p.s.i.; 50°). The reaction was stopped after the uptake of the theoretical amount of hydrogen (0.564 mol), then it was filtered to remove the catalyst and the solvent was evaporated under reduced pressure. After the residue was taken up in water (400 ml) and toluene (200 ml), the mixture was heated to reflux and then made basic with 10N sodium hydroxide. The mixture was cooled to 5°, and the resulting solid was collected by filtration, then was washed in turn with water, toluene, toluene-hexane (1:1) and hexane to give, after drying, 62.5 g of alpha,alpha-bis(3-methoxyphenyl)-4-piperidineethanol, mp 111°-113°.

Workup

  1. filtrationit was filtered
  2. customto remove the catalyst
  3. customthe solvent was evaporated under reduced pressure
  4. temperaturetoluene (200 ml), the mixture was heated
  5. temperatureto reflux
  6. temperatureThe mixture was cooled to 5°
  7. filtrationthe resulting solid was collected by filtration
  8. washwas washed in turn with water, toluene, toluene-hexane (1:1) and hexane
  9. customto give
  10. customafter drying

Sources & evidence

ORD record
ord-b7ac4194b362458a80e44120ed9a5ad1
Source dataset
uspto-grants-1986_12
Patent number
US04632925

Reaction notes

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