2-(2-Fluorophenyl)ethylamine → N-[2-(2-fluorophenyl)ethyl]-N-[4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]amine

Temperature

60 °C

To a solution of 4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzaldehyde (32.8 mg, 0.1 mmol) in anhydrous THF (0.6 mL) was added the 2-(2-fluorophenyl)ethylamine (11.8 mg, 0.1 mmol) and Ti(iPrO)4 (0.035 mL, 0.12 mmol). The mixture was stirred for 3 h at 60° C. then sodium triacetoxyborohydride (53 mg, 0.25 mmol) was added and the reaction mixture was stirred overnight at rt. THF (0.75 mL) was added followed by the PS-DEAM resin (Argonaut, 148 mg, 1.68 mmol/g), and the reaction mixture was stirred at rt overnight. The reaction mixture was filtered and the filtrates were eluted through a SCX column (Isolute, 1 g) with DCM (6 mL), then NH3 (2M in MeOH, 4 mL). The desired fractions (TLC monitoring) were concentrated under vacuum to give the title product.

1. stirringthe reaction mixture was stirred overnight at rt
2. stirringthe reaction mixture was stirred at rt overnight
3. filtrationThe reaction mixture was filtered
4. washthe filtrates were eluted through a SCX column (Isolute, 1 g) with DCM (6 mL)
5. concentrationThe desired fractions (TLC monitoring) were concentrated under vacuum

ORD record

ord-6a207b370cc54f93880620dbf7789bba

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592477B2