Reacción #80849

Ecuación de reacción

cyclohexylmethyl bromide

HCl

2-picolylamine

benzaldehyde

potassium hydroxide

→

racemic 1-(2-pyridyl)-2-cyclohexylethylamine

Rendimiento 45.0%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGwith stirring
2. 2
   TemperaturaThe mixture was refluxed for 6-24 hours
3. 3
   Temperaturacooled
4. 4
   Lavadothe aqueous acidic phase was washed with methylene chloride
5. 5
   Extracciónthe racemic amine extracted with methylene chloride

Procedimiento

A mixture of 2.16 g of 2-picolylamine (20 mmoles) and 2.12 g of benzaldehyde (20 mmoles) was stirred for 5-20 hours. The reaction mixture was diluted with 20 ml of toluene with stirring, then 1.12 g (20 mmoles) of potassium hydroxide added followed by the addition of 3.7 g of tetrabutylammonium iodide (10 mmoles) and 3.55 g of cyclohexylmethyl bromide (20 mmoles). The mixture was refluxed for 6-24 hours, then cooled and stirred with 10 ml of a 2N HCl for 2-6 hours. The organic phase was discarded, the aqueous acidic phase was washed with methylene chloride. The aqueous phase was basified with ammonium hydroxide and the racemic amine extracted with methylene chloride to yield 45%-55% racemic 1-(2-pyridyl)-2-cyclohexylethylamine as a light yellow oil.

Fuente