Reaktion #667802

Reaktionsgleichung

Phenyl glyoxal

2-(4-carbomethoxyphenyl)ethanamine

benzene

→

N-(2-[4-Carbomethoxyphenyl]ethyl)-2-hydroxy-2-phenylethanamine

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigehad been collected
2. 2
   workup.ADDITIONwas added portionwise with ice cooling
3. 3
   Sonstigethe solvent was evaporated
4. 4
   Sonstigethe residue was partitioned between water and ethyl acetate
5. 5
   ExtraktionThe dried organic extract
6. 6
   Sonstigewas evaporated
7. 7
   Sonstigecrystallised from benzene/hexane, mp 105°-106°

Vorschrift

Phenyl glyoxal (0.8 g) and 2-(4-carbomethoxyphenyl)ethanamine (1.1 g) were heated in refluxing benzene (100 ml) under a Dean and stark head until the theoretical amount of water had been collected. The solvent was replaced with methanol and sodium borohydride (2.0 g) was added portionwise with ice cooling. The mixture was stirred for 2 hours, the solvent was evaporated and the residue was partitioned between water and ethyl acetate. The dried organic extract was evaporated and crystallised from benzene/hexane, mp 105°-106°. (CDCl3) 6.80-7.60 (8H, m), 6.18 (3H, s), 5.34 (1H, m), 2.94 (2H, d, J=8 Hz), 2.77 (5H, m), 2.09 (2H, d, J=8 Hz).

Quelle