Pyrrolidine → 2-[2-(Pyrrolidin-1-yl)phenyl]acetic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 10.7 g of 2-(2-bromophenyl)acetic acid, 20 cm3 of pyrrolidine and 1.66 g of copper acetate is heated at 90° C. with stirring for 2 hours; after return to room temperature, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (0.2-0.063 mm, diameter 5 cm, height 55 cm), eluting with 1000 cm3 of 1,2-dichloroethane then with mixtures of 1,2-dichloroethane and methanol (proportions by volume): 1000 cm3 (98:2), 2000 cm3 (97:3), 1000 cm3 (96:4) and 1000 cm3 (95:5) and collecting fractions of 250 cm3. Fractions 21 to 29 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 2 g of 2-[2-(1-pyrrolidinyl)phenyl]acetic acid are obtained in the form of an orange-coloured oil.

Provenance & Evidence