反应详情

A solution of 3-chloro-4'-fluoropropiophenone (9.3 g, 0.05 mole) in 100 ml THF was treated with triethylamine (5.6 g, 0.055 mole) and stirred at room temperature for one hour. The mixture was treated with 2-naphthaleneethylamine hydrochloride (10.4 g, 0.05 mole) and refluxed for six hours. The reaction mixture was cooled to room temperature, and the resulting crystals were collected by filtration, washed with THF, ether, and water; and dried to give the title compound as a homogeneous product by tlc (chloroform-methanol, 9:1) (96%, 17.2 g); mp 208°-210° C.; IR(nujol): C=O @ 1675 cm-1 ; NMR(DMSO-d6, TMS): δ 3.20(t,2H, CH2 --CO), 3.37(m,4H,Ar--CH2 --CH2), 3.60(t,2H,N--CH2) [7.3-7.6(m,5H), 7.7-7.8(m,2H), 8.10(m,2H) aromatic]; Anal. Found: C,70.37; H,5.92; N,3.81. Mass spectrum m/e 321,184.

1. temperaturerefluxed for six hours
2. temperatureThe reaction mixture was cooled to room temperature
3. filtrationthe resulting crystals were collected by filtration
4. washwashed with THF, ether, and water
5. customand dried