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

HRID 1417816Notes

Reaction equation

HRID 1417816 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-4c145e999860484ca64935ecf80eb920
Source dataset
uspto-grants-1999_03
Patent number
US05877317

Reaction notes

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