Reaktion #360065

Reaktionsgleichung

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

potassium carbonate

→

title compound

Ausbeute 45.7%

1-{4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-ylmethyl}pyrrolidine

Ausbeute 45.7%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthen concentrated under reduced pressure
2. 2
   SonstigeThe crude product was purified by column chromatography on silica gel eluting with DCM:MeOH:NH3 (94:5:1)

Vorschrift

To a stirred solution of {4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-yl}methylamine (150 mg, 0.47 mmol) and 1-bromo-4-chloroethane (54.2 μL, 0.47 mmol) in anhydrous acetonitrile (5 mL) was added potassium carbonate (65 mg, 0.47 mmol). The mixture was heated to 60° C. overnight then concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with DCM:MeOH:NH3 (94:5:1) to give the title compound (40 mg, 23% yield). 1H NMR (400 MHz, CDCl3) δ 7.20 (d, 2H), 6.86 (d, 2H), 4.02 (t, 2H), 3.73-3.78 (m, 2H), 3.57-3.53 (m, 2H), 2.65-2.61 (m, 4H), 2.53 (m, 4H), 2.20 (m, 4H), 2.10-1.88 (m, 6H), 1.56 (m, 4H).

Quelle