5-Hydroxy-1-methyl-3-(4-methylphenyl)-1,2,5,6-tetrahydropyridine → cis-3-Hydroxy-1-methyl-5-(4-methylphenyl)piperidine

HRID 2166573Notes

Reaction equation

HRID 2166573 reaction equation
[OH:1][CH:2]1[CH2:7][N:6]([CH3:8])[CH2:5][C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[CH:3]1.[H][H]>CO.[Pd]>[OH:1][C@H:2]1[CH2:3][C@@H:4]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH2:5][N:6]([CH3:8])[CH2:7]1

Participants

5

Reactant 2

HCID 129007105-Hydroxy-1-methyl-3-(4-methylphenyl)-1,2,5,6-tetrahydropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 70531150cis-3-Hydroxy-1-methyl-5-(4-methylphenyl)piperidineYield 77.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-hydroxy-1-methyl-3-(4-methylphenyl)-1,2,5,6-tetrahydropyridine (5.1 g, 25 mM) in methanol (200 ml) was hydrogenated in a Parr apparatus at 50 psi (about 3.51×104 kg/sq.m.) and room temperature over 10% palladium-on-charcoal (1 g). After the theoretical uptake of hydrogen had occurred (about 3 hours) the catalyst was removed by filtration and the solvent removed under vacuum. Recrystallisation from cyclohexane gave the title compound (4 g). A portion was converted to the hydrochloride and recrystallized from methanol/ether to give the title compound hydrochloride, m.p. 218°-9°.

Workup

  1. custom(about 3 hours)
  2. customwas removed by filtration
  3. customthe solvent removed under vacuum
  4. customRecrystallisation from cyclohexane

Sources & evidence

ORD record
ord-49a0203df93e4b09ae3fba6f31236acf
Source dataset
uspto-grants-1983_06
Patent number
US04387230

Reaction notes

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