Methyl Ethyl Ketone → Ethyl 4-(2-Piperidinoethoxy)benzoate

Temperature

80 °C

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 monohydrochloride (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.

1. temperaturethe mixture was cooled to about 55° C.
2. temperatureThe resulting mixture was heated to 80° C
3. customwas consumed
4. customUpon complete reaction
5. temperatureto cool to room temperature
6. concentrationthe organic layer concentrated in vacuo at 40° C.
7. customThe resulting oil was used in the next step without further purification

ORD record

ord-0ce297b261d74b3d9e058303500aa2d3

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06472531B1