反应详情

3.9 g of benzoyl chloride and 2.1 g of ammonium thiocyanate are introduced into anhydrous acetone in a three-necked flask under argon and maintained between 0° and 5° C., the reaction mixture is left stirring for 15 minutes and then 3.9 g of N-naphth-1-yl-N-propylamine, dissolved in acetone, are added dropwise. The reaction mixture is then heated at reflux for 1 hour and evaporated to dryness and the residue is taken up in concentrated hydrochloric acid, heated at reflux for 3 hours and allowed to return to room temperature. The organic products are extracted with diethyl ether and then successively basification is carried out with 33% sodium hydroxide, extraction is carried out with ethyl acetate, the organic phase is evaporated to dryness and the residue is purified on a column of silica gel eluted with a 75/25 (v/v) hexane/ethyl acetate mixture, to obtain 3.2 g of white crystals melting at 170°-171° C. 1H NMR (CDCl3): 0.86 (t, J=7.3, 3H, --CH2 --CH3), 1.68 (m, 2H, --CH2 --CH3), 3.72 (m, 2H, --CH2 --CH2 --CH3), 5.58 (m, 2H, --NH2), 7.37 (d, J=7.3, 1H, H2), 7.23 (m, 2H, H3 and H8), 7.75-7.80 (m, 2H, H6 and H7), 7.85-7.95 (m, 2H, H4 and H5).

1. temperaturemaintained between 0° and 5° C.
2. waitthe reaction mixture is left
3. additionare added dropwise
4. temperatureThe reaction mixture is then heated
5. temperatureat reflux for 1 hour
6. customevaporated to dryness
7. temperatureheated
8. temperatureat reflux for 3 hours
9. customto return to room temperature
10. extractionThe organic products are extracted with diethyl ether
11. extractionsuccessively basification is carried out with 33% sodium hydroxide, extraction
12. customthe organic phase is evaporated to dryness
13. customthe residue is purified on a column of silica gel
14. washeluted with a 75/25 (v/v) hexane/ethyl acetate mixture