Reacción #1754

Ecuación de reacción

4-chlorobenzoylchloride

cis-4-(4-dimethylaminomethylphenyl)-cyclohexanol

triethylamine

dimethylaminopyridine

sodium hydroxide

→

cis-O-(4-Chlorobenzoyl)-4-(4-dimethylaminomethylphenyl)-cyclohexanol

Disolventes

water

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe methylene chloride phase is separated off
2. 2
   Extracciónthe aqueous phase is extracted several times with methylene chloride
3. 3
   Lavadothe combined organic phases are washed with saturated saline solution
4. 4
   Otrodried
5. 5
   Otroevaporated down in vacuo
6. 6
   OtroThe residue is purified by column chromatography (aluminium oxide neutral, activity stage III, ICN; petroleum ether/ethyl acetate=45:1) White crystals

Procedimiento

0.24 g (0.001 mol) of cis-4-(4-dimethylaminomethylphenyl)-cyclohexanol, 0,34 ml (0.0025 mol) of triethylamine and 0.12 g (0.001 mol) of dimethylaminopyridine are dissolved in 20 ml of methylene chloride, mixed with 0.175 g (0.001 mol) of 4-chlorobenzoylchloride and stirred for 12 hours at ambient temperature. The reaction mixture is combined with water and adjusted to pH 12-13 using sodium hydroxide solution. The methylene chloride phase is separated off, the aqueous phase is extracted several times with methylene chloride and the combined organic phases are washed with saturated saline solution, dried and evaporated down in vacuo. The residue is purified by column chromatography (aluminium oxide neutral, activity stage III, ICN; petroleum ether/ethyl acetate=45:1) White crystals.

Fuente