2,3-Dimethyliodobenzene → 4-n-Butyl-1-[4-(2,3-dimethylphenyl)-4-oxo-1-butyl]piperidine

Participants

Reaction Steps

In a 10 mL oven-dried flask was added Mg turnings (94 mg, 3.8 mmol) which was activated under vacuum by the use of a heat-gun. Under inert atmosphere was added a suspension of 1-iodo-2,3-dimethylbenzene (0.69 g, 3.0 mmol) in Et2O (5 mL) under spontaneously reflux, and the reaction mixture was allowed to reflux for 4 hours. A suspension of compound 4 (0.41 g, 2.0 mmol) in CH2Cl2 (2 mL) was added to the reaction mixture and left at rt overnight. The reaction mixture was quenched by addition of H2SO4 (7 mL, 2 M) and stirred at rt for 3 hours, followed by addition of NaOH (20 mL, 2 M) until basic conditions. The reaction mixture was extracted with ethyl acetate (3×50 mL) and the combined organic phases are washed with brine (10 mL) and NaOH (10 mL, 2 M), and the organic phases were dried (MgSO4) and evaporated to dryness to produce 0.69 g of crude 19. The crude product was subjected to CC [eluent: CH2Cl2 MeOH (99:1)] to give pure 19 (0.40 g, 64%); LC-MS [M+H]+ 315 (cald. 315.5).

Provenance & Evidence