反应详情

温度

110 °C

A mixture of 0.637 g (0.00175 mole) 4-(3-chloropropoxy)-3-methoxymandelic acid phenylmethyl ester, 0.545 g (0.00180 mole) of [α,α-bis(4-fluorophenyl)]-4-piperidinemethanol hydrochloride, and 0.3 ml (0.0025 mole) of triethylamine in 3 ml of benzyl alcohol was heated under nitrogen atmosphere at 110° C. for 7 hours while the reaction was monitored by TLC (silica gel, methylene chloride/methanol/ammonium hydroxide 90:10:1). The reaction mixture was concentrated in vacuo, ethyl ether (60 ml) and hexanes (40 ml) were added to the oily residue, and the solution was kept in the refrigerator for 2 hours. The solid that formed was filtered, washed with ether and dissolved in methylene chloride (40 ml). The methylene chloride solution was washed with water (3×10 ml) and dried (sodium sulfate), and the solvent was evaporated in vacuo to give 0.6 g of an oil. Final purification was done using 6 tapered silica gel plates 20×20 cm eluting with methylene chloride/methanol/ammonium hydroxide (90:5:0.5). The TLC sections containing the product were scraped off, and eluted with the above solvent system to give 0.4 g (34%) of the product as a light-amber oil. 1H NMR and mass spectral analysis support the structure assigned.

1. concentrationThe reaction mixture was concentrated in vacuo, ethyl ether (60 ml) and hexanes (40 ml)
2. additionwere added to the oily residue
3. customThe solid that formed
4. filtrationwas filtered
5. washwashed with ether
6. dissolutiondissolved in methylene chloride (40 ml)
7. washThe methylene chloride solution was washed with water (3×10 ml)
8. dry with materialdried (sodium sulfate)
9. customthe solvent was evaporated in vacuo