Benzaldehyde → N-benzyl-1-(3,4-dimethoxyphenyl)ethanamine

HRID 704838Notes

Reaction equation

HRID 704838 reaction equation
[NH2:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1)[CH3:3].[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[BH4-].[Na+]>N1C=CC=CC=1.CO>[CH3:13][O:12][C:6]1[CH:5]=[C:4]([CH:2]([CH3:3])[NH:1][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=[CH:8][C:7]=1[O:10][CH3:11]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 31592431-(3,4-Dimethoxyphenyl)ethan-1-amineHCID 4311764Sodium borohydride

Product 1

HCID 2756621N-benzyl-1-(3,4-dimethoxyphenyl)ethanamineYield 100%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 887MethanolSolvent

Procedure

A mixture containing 18.1 g of 1-amino-1-(3,4-dimethoxyphenyl)-ethane (J. Chem. Soc. 1963, 4289), 10,6 g of benzaldehyde and 1 drop of pyridine in 100 ml of methanol is let stand at 20° C. for 2 days, then 3.8 g of sodium borohydride are added during 30 minutes and stirred for additional 3 hours. After evaporation of the solvent, the residue is diluted with water, extracted with chloroform, the organic phase is dried and evaporated to give 27.1 g of the crude title compound, which can directly be used in the process described in Example 6.

Workup

  1. customAfter evaporation of the solvent
  2. additionthe residue is diluted with water
  3. extractionextracted with chloroform
  4. customthe organic phase is dried
  5. customevaporated

Sources & evidence

ORD record
ord-410bde7194ba4142b2429f990e3a0d04
Source dataset
uspto-grants-1991_01
Patent number
US04988730

Reaction notes

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