Réaction #2879

Équation de réaction

1-(2-chloroethyl)piperidine hydrochloride

ethyl 4-hydroxybenzoate

1-(2-chloroethyl)piperidine monohydrochloride

potassium carbonate

methyl ethyl ketone

1-(2-chloroethyl)piperidine mono-hydrochloride

→

Ethyl 4-(2-Piperidinoethoxy)benzoate

Solvants

water

ethyl acetate acetonitrile triethylamine

Conditions de réaction

Traitement

1. 1
   Températurethe mixture was cooled to about 55° C.
2. 2
   TempératureThe resulting mixture was heated to 80° C
3. 3
   Autrewas consumed
4. 4
   AutreUpon complete reaction
5. 5
   Températureto cool to room temperature
6. 6
   Concentrationthe organic layer concentrated in vacuo at 40° C.
7. 7
   AutreThe resulting oil was used in the next step without further purification

Mode opératoire

A mixture of ethyl 4-hydroxybenzoate (8.31 g), 1-(2-chloroethyl)piperidine monohydrochloride (10.13 g), potassium carbonate (16.59 g), and methyl ethyl ketone (60 mL) was heated to 80° C. After one hour, the mixture was cooled to about 55° C. and treated with additional 1-(2-chloroethyl)piperidine mono-hydrochloride (0.92 g). The resulting mixture was heated to 80° C. The reaction was monitored by thin layer chromatography (TLC), using silica-gel plates and ethyl acetate/acetonitrile/triethylamine (10:6:1, v/v). Additional portions of 1-(2-chloroethyl)piperidine hydrochloride were added until the starting 4-hydroxybenzoate ester was consumed. Upon complete reaction, the reaction mixture was treated with water (60 mL) and allowed to cool to room temperature. The aqueous layer was discarded and the organic layer concentrated in vacuo at 40° C. and 40 mm Hg. The resulting oil was used in the next step without further purification.

Source