Reaction #1939

Reaction equation

hydrochloric ether

BOP

compound

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

phenylacetic acid

→

hydrochloride

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

Solvents

DCM

triethylamine

DCM

Conditions

Workup

1. 1
   ConcentrationThe resulting mixture is concentrated under vacuum
2. 2
   Washwashed with water, with 1N NaOH solution and with saturated NaCl solution
3. 3
   Dryingdried over MgSO4
4. 4
   Concentrationconcentrated under vacuum
5. 5
   OtherThe residue is chromatographed on silica gel H
6. 6
   OtherThe product obtained
7. 7
   Concentrationconcentrated under vacuum

Procedure

0.46 ml of triethylamine and then 0.5 g of BOP are added to a mixture of 0.5 g of the compound obtained in EXAMPLE 11, step B), 0.127 g of phenylacetic acid and 10 ml of DCM. The resulting mixture is concentrated under vacuum and the residue is taken up with AcOEt, washed with water, with 1N NaOH solution and with saturated NaCl solution, 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 0.42 g of the expected hydrochloride after crystallization from iso ether. M.p.=125° C.

Source