Sampirtine synthesis
- Product Name:Sampirtine
- CAS Number:115911-28-9
- Molecular formula:C12H12FN3
- Molecular Weight:217.24
Yield:115911-28-9 58%
Reaction Conditions:
with ammonia in dichloromethane;
Steps:
1 2,6-diamino-3-(4-fluoro)benzylpyridine (D 17033)
EXAMPLE 1 2,6-diamino-3-(4-fluoro)benzylpyridine (D 17033) 10.9 g (0.1M) of 2,6-diaminopyridine are melted by gradual warming and 14.45 g (0.1M) of 4-fluorobenzylchloride are added dropwise at 115°-120° C. After the reaction has heated exothermically up to about 140°-160° C., heating is continued for a further approximately 4 hours at 130°-150° C., after which the reaction vessel is cooled and the syrupy mixture is dissolved in 400 ml of methylene chloride and about 40 ml of concentrated ammonia. The reaction mixture is extracted with water and the organic phase is then separated off and dried over anhydrous sodium sulphate. The solvent is evaporated off in a vacuum and the remaining residue is separated by column chromatography (Geduran Si 60 from Merck AG, Darmstadt, eluding solvent: methylene chloride/ethanol--9:1% by volume). There are obtained 12.6 g of 2,6-diamino-3-(4-fluoro)benzylpyridine with a melting point of 123°-124° C. (Yield 58% of theory). Thin layer chromatography: RF -value: 0.34 Eluding solvent: methylene chloride/ethanol/concentrated ammonia=95:4:1% by volume). Following evaporation of the solvent, the remaining residue may also be purified by fractionated distillation in a high vacuum (B.p.: 190°-210° C. at 0.4 m bar)
References:
US4851420,1989,A
