Triethylamine → (4-Bromo-2,6-dimethyl-phenyl)-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Participants

Reaction Conditions

Reaction Steps

A suspension of 0.344 g (1.5 mmol) 4-bromo-2,6-dimethyl-benzoic acid [Fuson, R. C.; Scott, S. L.; Lindsey, R. V., Jr. Journal of the American Chemical Society (1941), 63, 1679-82] in 5 ml of CH2Cl2 was treated at RT with two drops of DMF; then, a solution of 0.14 ml=0.21 g (1.6 mmol) of oxalyl chloride in 3 ml of CH2Cl2 was added drop by drop below 25° C. and the reaction mixture was stirred of 1 hour. After removal of the solvents by evaporation in a high vacuum, the residue was dissolved again in 10 ml of CH2Cl2 and the solution cooled down to 0° C.; then, 0.42 ml=0.30 g (3.0 mmol) of Et3N was added while stirring, followed by 0.23 g (1.5 mmol) of 4-pyrrolidin-1-yl-piperidine. The reaction mixture was subsequently warmed up to RT. After 60 hours, it was poured into crashed ice and extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 95:5) to give 0.42 g (76%) of the title compound as light yellow oil. MS: 365.0 (MH+, 1 Br).

Provenance & Evidence