Benzaldehyde → HCID 10890003, compound

HRID 1585816Notes

Reaction equation

HRID 1585816 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C@@H:17]([NH2:19])[CH3:18])=[CH:13][CH:12]=1>ClCCl>[CH:1](=[N:19][C@H:17]([C:14]1[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=1)[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 793467(S)-1-(4-Methoxyphenyl)ethylamine

Product 1

HCID 10890003HCID 10890003, compoundYield 106.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 5.6 g of benzaldehyde in 25 cm3 of dichloromethane are added, with stirring and at a temperature in the region of 20° C., 8.5 g of (S)-1-(4-methoxyphenyl) ethylamine and 5 g of 4 Å 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 3 times with 20 cm3 of dichloromethane and the filtrates are combined and then concentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C. 13.4 g of (S)-N-benzylidene-[1-(4-methoxyphenyl)-ethylamine] are thus obtained, in the form of a light brown oil.

Workup

  1. filtrationfiltered through a sinter funnel
  2. additioncontaining Celite
  3. washThe sinter funnel is washed 3 times with 20 cm3 of dichloromethane
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-5cee4b3b9eef4ca0b725c45ae93b5f4b
Source dataset
uspto-grants-1999_08
Patent number
US05939561

Reaction notes

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