Réaction #414595

Équation de réaction

alcohol

4-(3-Quinolinyl)-3-butyn-1-ol

N,N-diisopropylethylamine

4-phenyl-1,2,3,6-tetrahydropyridine

sodium bicarbonate

methanesulfonyl chloride

→

title compound

3-[4-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butynyl]-quinoline

Conditions de réaction

Traitement

1. 1
   Concentrationconcentrated under reduced pressure
2. 2
   TempératureThe mixture is heated at 40° C. for 5 hours
3. 3
   Autrethe solvent is removed under reduced pressure
4. 4
   AutreThe residue is partitioned between 50 mL of ethyl acetate and 50 mL of water
5. 5
   ExtractionThe aqueous layer is extracted with 50 mL of ethyl acetate
6. 6
   Séchagethe combined organic layers are dried (sodium sulfate)
7. 7
   Autrethe solvent is removed in vacuo
8. 8
   AutreThe residue is chromatographed (silica gel, 2% methanol/98% dichloromethane)

Mode opératoire

A solution of the alcohol prepared in Step (a) (1.98 g, 0.01 mol), N,N-diisopropylethylamine (3.5 mL, 0.02 mol) and a catalytic amount of 4-dimethylaminopyridine is cooled to 0° C., and methanesulfonyl chloride (0.8 mL, 0.0105 mol) is added dropwise. The solution is stirred at 0° C. for 18 hours, and then concentrated under reduced pressure. The residue is taken up in dimethylformamide (20 mL), and to this solution is added 4-phenyl-1,2,3,6-tetrahydropyridine (2.41 g, 0.015 mol) and sodium bicarbonate (3.4 g, 0.04 mol). The mixture is heated at 40° C. for 5 hours, and the solvent is removed under reduced pressure. The residue is partitioned between 50 mL of ethyl acetate and 50 mL of water. The aqueous layer is extracted with 50 mL of ethyl acetate and the combined organic layers are dried (sodium sulfate), and the solvent is removed in vacuo. The residue is chromatographed (silica gel, 2% methanol/98% dichloromethane) to give the title compound, containing 0.4 mol of water; mp 94.3°-95.8° C.

Source