Реакция #667802

Уравнение реакции

Phenyl glyoxal

2-(4-carbomethoxyphenyl)ethanamine

benzene

→

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

Растворители

water

Условия реакции

Обработка

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

Методика

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).

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