Réaction #215959

Équation de réaction

valeryl chloride

2-(2-methoxy-1-naphthyl)ethylamine

triethylamine

potassium hydroxide

chloride

→

N-[2-(2-methoxynaphthyl)ethyl]pentanamide

Rendement 46.8%

Solvants

dichloromethane

water

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONis introduced into a 100-cm3 two-necked flask under an inert atmosphere
2. 2
   TempératureThe mixture is cooled with an ice bath
3. 3
   workup.ADDITIONis introduced
4. 4
   AutreAfter the introduction of the reactants, the ice bath is removed
5. 5
   Autrereaction
6. 6
   ExtractionAfter extraction three times with dichloromethane
7. 7
   Séchagethe organic phase is dried over magnesium sulfate
8. 8
   AutreAfter evaporation of the solvent and recrystallization of the solid
9. 9
   Autreobtained, in the heated state, in a pentane/ethyl acetate mixture

Mode opératoire

0.59 g (2.93 mmol) of 2-(2-methoxy-1-naphthyl)ethylamine, which is solubilized in 20 cm3 of anhydrous dichloromethane, is introduced into a 100-cm3 two-necked flask under an inert atmosphere. The mixture is cooled with an ice bath and stirred, and 0.61 cm3 (4.37 mmol) of triethylamine dried over potassium hydroxide, is introduced, followed by 0.42 cm3 (3.54 mmol) of valeryl chloride. After the introduction of the reactants, the ice bath is removed and reaction is allowed to proceed at room temperature for 30 min. Hydrolysis of the excess chloride is carried out by pouring the reaction mixture into water. After extraction three times with dichloromethane, the organic phase is dried over magnesium sulfate. After evaporation of the solvent and recrystallization of the solid obtained, in the heated state, in a pentane/ethyl acetate mixture, 0.39 g (1.37 mmol) of N-[2-(2-methoxynaphthyl)ethyl]pentanamide (white solid) is obtained, equivalent to a yield after purification of 47%.

Source