Réaction #80849

Équation de réaction

cyclohexylmethyl bromide

HCl

2-picolylamine

benzaldehyde

potassium hydroxide

→

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

Rendement 45.0%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGwith stirring
2. 2
   TempératureThe mixture was refluxed for 6-24 hours
3. 3
   Températurecooled
4. 4
   Lavagethe aqueous acidic phase was washed with methylene chloride
5. 5
   Extractionthe racemic amine extracted with methylene chloride

Mode opératoire

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.

Source