Reaction #1754

Reaction equation

4-chlorobenzoylchloride

cis-4-(4-dimethylaminomethylphenyl)-cyclohexanol

triethylamine

dimethylaminopyridine

sodium hydroxide

→

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

Solvents

water

methylene chloride

Conditions

Workup

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

Procedure

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.

Source