反应详情

A mixture of N,N-dimethyl-3-hydroxy-3-phenylpropylamine (3.58 g, 20 mM), 50% sodium hydride dispersion (1 g) and DMSO (50 ml) was heated at 80° until homogenous, cooled to ambient temperature and treated dropwise with a solution of 4-fluorobenzonitrile (2.42 g, 20 mM) in DMSO with cooling (exothermic). After 1 h the reaction mixture was poured on to water (200 ml) and extracted with ether (2×200 ml). The ether extract was extracted with 1 N hydrochloric acid (2×50 ml), the acid extract basified and then extracted with ether (2×200 ml). The ether was dried and the solvents removed under reduced pressure to give an oil which was dissolved in ethyl acetate and treated with an excess of a solution of oxalic acid dihydrate in ethyl acetate. Removal of the resultant precipitate by filtration followed by recrystallisation from ethyl acetate gave the title compound (4.8 g) as the oxalate quarter hydrate m.p. 80° (decomp). Found: C, 64.1; H, 6.05; N, 7.7% C18H20N2O.C2H2O4 requires: C, 64.1; H, 6.1; N 7.5%.

1. temperaturewas heated at 80° until homogenous,
2. temperaturewith cooling (exothermic)
3. extractionextracted with ether (2×200 ml)
4. extractionThe ether extract
5. extractionwas extracted with 1 N hydrochloric acid (2×50 ml)
6. extractionthe acid extract
7. extractionextracted with ether (2×200 ml)
8. dry with materialThe ether was dried
9. customthe solvents removed under reduced pressure
10. customto give an oil which
11. customRemoval of the resultant precipitate
12. filtrationby filtration
13. customfollowed by recrystallisation from ethyl acetate