2-Thiophenecarboxaldehyde → 1-(3,4-Dimethoxyphenyl)ethan-1-amine

HRID 1585818Notes

Reaction equation

HRID 1585818 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@H:11]([NH2:13])[CH3:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].S1C=CC=C1C=O>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH2:13])[CH3:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 73642-ThiophenecarboxaldehydeHCID 376091(1s)-1-(3,4-dimethoxyphenyl)ethanamine

Product 1

HCID 31592431-(3,4-Dimethoxyphenyl)ethan-1-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 43.8 g of (S)-1-(3,4-dimethoxyphenyl)ethylamine in 400 cm3 of dichloromethane are added, with stirring at a temperature in the region of 20° C., 16.8 cm3 of 2-thiophenecarboxaldehyde and 35 g of 4Å molecular sieves. The reaction mixture is stirred for 16 hours at a temperature in the region of 20° C., and then filtered through a sinter funnel containing Celite. The sinter funnel is washed with 3 times 50 cm3 of dichloromethane and the filtrates are combined and then concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. 45.95 g of (S)-N-(2-thienyl)-methylidene]-[1-(3,4-dimethoxyphenyl)ethylamine are thus obtained in the form of a colourless oil for which the characteristics are the following:

Workup

  1. filtrationfiltered through a sinter funnel
  2. additioncontaining Celite
  3. washThe sinter funnel is washed with 3 times 50 cm3 of dichloromethane
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C

Sources & evidence

ORD record
ord-c03228919f6f4c2881d27cfbf7c44928
Source dataset
uspto-grants-1999_08
Patent number
US05939561

Reaction notes

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