Benzaldehyde → N-Benzyl-2-(3,4-dimethoxyphenyl)-N-methylethan-1-amine

HRID 1087997Notes

Reaction equation

HRID 1087997 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH2:6][CH2:7][NH2:8].[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C=O.[CH2:24](O)C>[Pd].C(O)C.C(Cl)Cl>[CH2:14]([N:8]([CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 702EthanolHCID 712FormaldehydeHCID 8421Homoveratrylamine

Product 1

HCID 13424654N-Benzyl-2-(3,4-dimethoxyphenyl)-N-methylethan-1-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584144Dichloromethane ethanolSolvent

Procedure

In the first step 3,4-dimethoxyphenethylamine, benzaldehyde and formaldehyde are hydrogenated in the presence of a catalyst, e.g. palladium on carbon, either at normal or slightly elevated pressure, preferably a pressure of 2-3 atm (0.2-0.3 MPa), and the temperature is room temperature or slightly elevated temperature, preferably 20°-30° C. As solvent is used an organic solvent, e.g. ethanol or an ethanol-methylenechloride (1:1)-mixture. The desired product, N-benzyl-N-methyl-3,4-dimethoxyphenethylamine (II) is obtained in a very pure state, when it is precipitated as an acid addition salt, e.g. hydrobromide. As free base the product is oily and difficult to handle.

Workup

  1. customis room temperature
  2. customslightly elevated temperature, preferably 20°-30° C

Sources & evidence

ORD record
ord-4978a55266074066bc871364a218b1ef
Source dataset
uspto-grants-1990_10
Patent number
US04960939

Reaction notes

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