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0 °C

Ethylene diamine (30 mg, 0.5 mmol) was dissolved in dry ethanol (1.9 ml). The solution was cooled to 0° C. and 2-(2-chloro-3-ethynyl-phenoxy)-butyrimidic acid methyl ester (100 mg, 0.4 mmol) was added. After 1 h a solution of concentrated HCl (few drops) in ethanol (0.9 ml) was added and the reaction mixture was stored overnight at 0° C. The reaction mixture was then diluted with a further portion of ethanol (1.6 ml) and heated to 75° C. for 5 h. After cooling to room temperature a precipitate was formed that was filtered and discarded. The filtrate was evaporated and treated with CHCl3. Another precipitate was formed, which was filtered again. Finally, the CHCl3 phase was evaporated to yield 2-[1-(2-chloro-3-ethynyl-phenoxy)-propyl]-4,5-dihydro-1H-imidazole; 1H-NMR (CDCl3) 1.08 t, 3H, 1.9-2.1 m, 2H, 3.10-3.9, vbr s, 4H, 3.39, s, 1H, 4.85 dd, 1H, 7.05 d, 1H, 7.1-7.2, m, 2H.

1. temperatureheated to 75° C. for 5 h
2. temperatureAfter cooling to room temperature a precipitate
3. customwas formed
4. filtrationthat was filtered
5. customThe filtrate was evaporated
6. additiontreated with CHCl3
7. customAnother precipitate was formed
8. filtrationwhich was filtered again
9. customFinally, the CHCl3 phase was evaporated