反应详情

A solution of 8.0 g (0.022 mole) of 2-chloro-1-[5-(2,4-dichlorobenzoyl)-1,2,4-trimethyl-1H-pyrrol-3-yl]-ethanone (6) and 4.64 mL (0.066 mole) of piperidine in 130 mL of 2-propanol was heated under reflux for 1.5 h. The reaction was cooled and the solvent evaporated in vacuo. The residue was partitioned between diethyl ether and water and the organic solution was extracted twice with 1N HCl. A solid was removed by filtration and the filtrate was made basic with sodium bicarbonate. The mixture was extracted with diethyl ether and the ether solution was washed with water, brine and dried (MgSO4). The solvent was evaporated in vacuo. The product was converted to the hydrochloride salt and recrystallized from 2-propanol to give 5.97 g of product: mp 177-179° C.; mass spectrum (Cl—CH4) m/z=393 (m+1); NMR 300 MHz (Me2SO-d6) d 7.85 (s,1H); 7.6-7.5 (m, 2 H); 4.7 (s, 2 H); 3.8 (s, 3 H); 3.6-3.4 (m, 2 H); 3.2-3.0 (m, 2 H); 2.6 (s, 3H); 2.0 (br s, 4 H); 1.8 (s 3 H). Anal Calcd for C20H22Cl2N2O2: C, 55.22; H, 5.87; N, 6.05. Found: C, 55.06; H, 5.89; N, 6.05.

1. temperatureunder reflux for 1.5 h
2. temperatureThe reaction was cooled
3. customthe solvent evaporated in vacuo
4. customThe residue was partitioned between diethyl ether and water
5. extractionthe organic solution was extracted twice with 1N HCl
6. customA solid was removed by filtration
7. extractionThe mixture was extracted with diethyl ether
8. washthe ether solution was washed with water, brine
9. dry with materialdried (MgSO4)
10. customThe solvent was evaporated in vacuo
11. customrecrystallized from 2-propanol