Réaction #413733

Équation de réaction

3-butynyl tosylate

1-(2-pyridinyl)piperazine

sodium bicarbonate

dimethylformamide

→

title compound

4-[(2-pyridyl)-1-piperazinyl]-1-butyne

Conditions de réaction

Traitement

1. 1
   AutreThe solvent is removed under reduced pressure
2. 2
   Autrethe residue is partitioned between 200 mL of dichloromethane and 200 mL of water
3. 3
   ExtractionThe aqueous layer is extracted with 100 mL of dichloromethane
4. 4
   Séchagethe combined organic layers are dried (sodium sulfate)
5. 5
   Autrethe solvent is removed in vacuo
6. 6
   AutreThe residue is chromatographed (silica gel, 25% ethyl acetate/75% hexane)

Mode opératoire

A solution of 3-butynyl tosylate (25.0 g, 0.11 mol), 1-(2-pyridinyl)piperazine (12.1 g, 0.074 mol), and sodium bicarbonate (6.9 g, 0.082 mol) in 200 mL of dimethylformamide is heated at 80° C. for 18 hours. The solvent is removed under reduced pressure, and the residue is partitioned between 200 mL of dichloromethane and 200 mL of water. The aqueous layer is extracted with 100 mL of dichloromethane and the combined organic layers are dried (sodium sulfate), and the solvent is removed in vacuo. The residue is chromatographed (silica gel, 25% ethyl acetate/75% hexane) to give the title compound as a white solid; mp 57°-58° C.

Source