Reaktion #360069

Reaktionsgleichung

{4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-yl}methylamine

triethylamine

α-toluenesulfonylchloride

→

title compound

Ausbeute 69.7%

C-Phenyl-N-{4-[4-(3-pyrrolidin-1-yl-propoxy)-phenyl]-tetra-hydropyran-4-ylmethyl}-methanesulfonamide

Ausbeute 69.7%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction mixture was quenched with a saturated aqueous solution of NaHCO3
2. 2
   SonstigeThe organic layer was separated
3. 3
   Waschenwashed with water
4. 4
   Trocknendried over magnesium sulphate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under reduced pressure

Vorschrift

To a stirred solution of {4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-yl}methylamine (200 mg, 0.628 mmol) and triethylamine (106 μL, 0.754 mmol) in anhydrous dichloromethane (8 mL) under nitrogen atmosphere was added dropwise a solution of α-toluenesulfonylchloride (143 mg, 0.754 mmol) in anhydrous dichloromethane (2 mL). After stirring overnight, the reaction mixture was quenched with a saturated aqueous solution of NaHCO3. The organic layer was separated and washed with water, dried over magnesium sulphate, filtered and concentrated under reduced pressure to give the title compound (207 mg, 69%). 1H NMR (400 MHz, CDCl3) δ7.27-7.22 (m, 3H), 7.16-7.14 (m, 2H), 7.07 (d, 2H), 6.83 (d, 2H), 4.05 (s, 2H), 3.95 (t, 2H), 3.68-3.63 (m, 2H), 3.55 (t, 1H), 3.49-3.44 (m, 2H), 3.01 (d, 2H), 2.57 (t, 2H), 2.47 (s, 4H), 2.02-1.93 (m, 4H), 1.78-1.72 (m, 6H).

Quelle