Hydrochloric Acid → HCID 68294367, compound

Participants

Reaction Steps

A solution of 356 (4.54 g, 12.78 mmol) and concentrated HCl (106.5 mL, 1278 mmol) was heated to reflux and stirred over the weekend. The reaction mixture was then cooled to RT, transferred to separatory funnel, and washed with Et2O (1×200 mL). The aqueous layer was concentrated in a rotovap under high vacuum. The resulting solids were dissolved in 10% NaOH (20.45 g, 51.12 mmol). To the solution was added dioxane (30 mL) followed by Boc2O (2.929 g, 13.42 mmol). After stirring overnight, the reaction was diluted with H2O (100 mL) and washed with ether (1×100 mL). The aqueous layer was acidified with solid KHSO4 and then extracted with DCM (200 mL). The combined extracts were dried (MgSO4), filtered, concentrated and dried under high vacuum to afford 1.98 g (41%) of 1-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)piperidine-4-carboxylic acid (358) as a white foam.

Provenance & Evidence