alpha,alpha-Bis(4-methoxyphenyl)-1-(phenylmethyl)-4-piperidinemethanol → alpha,alpha-Bis(4-methoxyphenyl)-4-piperidinemethanol

HRID 345471Notes

Reaction equation

HRID 345471 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)([CH:11]2[CH2:16][CH2:15][N:14](CC3C=CC=CC=3)[CH2:13][CH2:12]2)[OH:10])=[CH:5][CH:4]=1>C(O)C.[Pd]>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[OH:10])=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 14698738alpha,alpha-Bis(4-methoxyphenyl)-1-(phenylmethyl)-4-piperidinemethanol

Product 1

HCID 14698742alpha,alpha-Bis(4-methoxyphenyl)-4-piperidinemethanolYield 30%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 36.7 g (0.088 mole) of α,α-bis(4-methoxyphenyl)-1-(phenylmethyl)-4-piperidinemethanol in 500 ml of absolute ethanol was hydrogenated over 1 tsp of 5% Pd/C at 60° C. in a Parr apparatus over the weekend. The mixture was cooled, filtered through Celite®, fresh catalyst added to the filtrate and the process repeated until no starting material was present by mass spectral analysis. The filtrate was concentrated and the residue was partitioned between methylene chloride and a 5% sodium hydroxide solution. The organic layer was dried over sodium sulfate and concentrated to give a solid residue. The solid was recrystallized from 2-propanol to yield 8.6 g (30%) of white solid, mp 153°-155° C.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through Celite®, fresh catalyst
  3. additionadded to the filtrate
  4. concentrationThe filtrate was concentrated
  5. customthe residue was partitioned between methylene chloride
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated
  8. customto give a solid residue
  9. customThe solid was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-207f2d00f0d24fbea7a2b5824d3b3ab4
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

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