Réaction #1939

Équation de réaction

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

Solvants

DCM

triethylamine

DCM

Conditions de réaction

Traitement

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

Mode opératoire

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