Reacción #214097

Ecuación de reacción

1-naphthoyl chloride

trans-1-cyclohexyl-4-methylamino-3-pyrrolidinol

potassium carbonate

→

Trans-N-(1-cyclohexyl-4-hydroxypyrrolidin-3-yl)-N-methyl-1-naphthalenecarboxamide Hydrochloride

Rendimiento 56.0%

Disolventes

methylene chloride

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Temperaturaheated
3. 3
   Temperaturaat reflux for 24 hrs
4. 4
   TemperaturaAfter cooling
5. 5
   Lavadothe mixture was washed with water
6. 6
   Otrothe organic fraction was evaporated under vacuum
7. 7
   OtroThe residue was chromatographed on silica gel
8. 8
   Lavadoeluting with acetone
9. 9
   OtroTen grams of the base, 56% yield, were collected
10. 10
    OtroAfter recrystallization from isopropyl alcohol

Procedimiento

A solution of 10 g (0.05 mole) of trans-1-cyclohexyl-4-methylamino-3-pyrrolidinol in 100 ml of methylene chloride was mixed with 10 g of powdered anhydrous potassium carbonate and stirred while a solution of 10 g (0.05 mole) of 1-naphthoyl chloride in 50 ml of methylene chloride was added dropwise. The mixture was stirred for 2 hrs and then heated at reflux for 24 hrs. After cooling, the mixture was washed with water and the organic fraction was evaporated under vacuum. The residue was chromatographed on silica gel, eluting with acetone. Ten grams of the base, 56% yield, were collected and converted to the hydrochloride. After recrystallization from isopropyl alcohol, the salt melted at 238°-241° C.

Fuente