Reaktion #479572

Reaktionsgleichung

N-(3-(2-methoxyphenoxy)phenyl)pyrid-3-ylmethylamine

2,2,2-trifluoroethylsulfonyl chloride

potassium carbonate

→

title compound

Ausbeute 50.0%

N-(3-(2-Methoxyphenoxy)phenyl)-N-(2,2,2-trifluoroethylsulfonyl)pyrid-3-ylmethylamine

Ausbeute 50.0%

Lösungsmittel

1,2-dichloroethane pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature
2. 2
   workup.STIRRINGstirred 30 min
3. 3
   Filtrationfiltered
4. 4
   Einengenthe filtrate concentrated in vacuo
5. 5
   SonstigeThe residue was chromatographed on silica gel (eluted with 2:1 dichloromethane/ethyl acetate)

Vorschrift

The resultant N-(3-(2-methoxyphenoxy)phenyl)pyrid-3-ylmethylamine was dissolved in 2:1 1,2-dichloroethane/pyridine (6 mL) under nitrogen, cooled (5° C.), and treated with 2,2,2-trifluoroethylsulfonyl chloride (300 mg, 1.64 mmol). After one hour at 5° C., the mixture was allowed to warm to room temperature and stirred for 18 h. The product mixture was treated with anhydrous potassium carbonate (500 mg), stirred 30 min, filtered, and the filtrate concentrated in vacuo. The residue was chromatographed on silica gel (eluted with 2:1 dichloromethane/ethyl acetate) to afford the title compound (226 mg, 50%) as a viscous pale amber oil. The hydrochloride salt was obtained by treatment of this material in methanol with ethereal HCl. 1H NMR: 8.49 (d,1H,J=4 Hz), 8.29 (s,1H), 7.60-7.65 (m,1H), 7.20-7.25 (m,2H), 7.10-7.20 (m,1H), 6.97 (d,1H,J=8 Hz), 6.90 (m,2H), 6.80-6.85 (m,2H), 6.76 (m,1H), 4.82 (s,2H), 3.70-3.85 (m,2H), 3.75 (s,3H). MS calcd. 452.4; MS (M+1) 453.3

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