Reaction #1938

Reaction equation

hydrochloric ether

triethylamine

compound

4-Acetamido-4-phenyl-1-[2-[1-(3,4-dichlorophenyl)-2-(N-methylamino)ethoxy]ethyl]piperidine dihydrochloride

benzyl chloroformate

→

hydrochloride

4-Acetamido-4-phenyl-1-[2-[1-(3,4-dichlorophenyl)-2-(N-methyl-N-benzyloxycarbonylamino)ethoxy]ethyl]piperidine hydrochloride

Solvents

DCM

DCM

Conditions

Workup

1. 1
   WashThe reaction mixture is washed twice with water
2. 2
   Dryingdried over MgSO4
3. 3
   Concentrationconcentrated under vacuum
4. 4
   OtherThe residue is chromatographed on silica gel H
5. 5
   OtherThe product obtained
6. 6
   Concentrationconcentrated under vacuum

Procedure

0.41 ml of triethylamine is added to a solution of 0.5 g of the compound obtained in EXAMPLE 11, step B), in 10 ml of DCM, the mixture is then cooled to 0° C. and 0.14 ml of benzyl chloroformate is added dropwise. The reaction mixture is washed twice with water, dried over MgSO4 and concentrated under vacuum. The residue is chromatographed on silica gel H using DCM and then a DCM/MeOH mixture (94/6; v/v) as the eluent. The product obtained is taken up with DCM, acidified to pH 1 by the addition of hydrochloric ether and concentrated under vacuum to give 0.39 g of the expected hydrochloride after crystallization from iso ether. M.p.=135° C.

Source