Hydrochloric Acid → 1-Benzyl-4-(4-methoxyphenyl)piperidine

HRID 368835Notes

Reaction equation

HRID 368835 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H].Cl>[Pd].CO.Cl>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 106364031-Benzyl-4-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 232889401-Benzyl-4-(4-methoxyphenyl)piperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 21893726Hydrochloride methanolSolvent

Procedure

Palladium on carbon (10%, 0.0695 g) is added to a mixture of 1-benzyl-1,2,3,6-tetrahydro-4-(4-methoxyphenyl)pyridine (XVI, Step 2, 0.6843 g, 2.4 mmol) in methanol/hydrochloric acid and the mixture is shaken overnight under approximately 40 psi of hydrogen. Additional palladium on carbon and concentrated hydrochloric acid are added and the mixture is again shaken overnight under hydrogen. The palladium on carbon then is filtered off and the filtrate is concentrated. The residue is partitioned between dichloromethane and saturated sodium bicarbonate and the combined organic phases are backwashed with saturated sodium bicarbonate, dried over magnesium sulfate, and concentrated to give 1-benzyl-4-(4-methoxyphenyl)piperidine (XVIII), NMR (CDCl3) 1.77, 2.07, 2.45, 3.00, 3.55, 3.78, 6.85, 7.16 and 7.31 δ.

Workup

  1. filtrationThe palladium on carbon then is filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe residue is partitioned between dichloromethane and saturated sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1239cf8f0efd4e65b916771a39d751cf
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Reaction notes

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