Hydrochloric Acid → 4-[(3,4-Dimethoxyphenyl)methyl]piperidine

HRID 1110797Notes

Reaction equation

HRID 1110797 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH:6]=[C:7]1[CH2:12][CH2:11][N:10](CC2C=CC=CC=2)[CH2:9][CH2:8]1.Cl>CO.C(O)(C)C.[OH-].[Pd+2].[OH-]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 14330294HCID 14330294, compound

Product 1

HCID 170394974-[(3,4-Dimethoxyphenyl)methyl]piperidineYield 98.2%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

4-(3,4-Dimethoxyphenylmethyl)piperidine is prepared by hydrogenation at 20° C., under two atmospheres, in the presence of palladium hydroxide (0.042 g), of 4-(3,4-dimethoxybenzylidene)-1-phenylmethylpiperidine (0.42 g) in methanol (100 cc), to which a 5N solution of hydrochloric acid in isopropanol (0.26 cc) has been added. After filtration and evaporation of the solvent under reduced pressure, 4-(3,4-dimethoxyphenylmethyl)-piperidine (0.3 g) is isolated in the form of a white solid whose melting point is 76° C.

Workup

  1. additionhas been added
  2. filtrationAfter filtration and evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-50ad30c8ab3f45098948b7bea62ef143
Source dataset
uspto-grants-1990_12
Patent number
US04977166

Reaction notes

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