Ammonia → HCID 21940701, compound

Participants

Reaction Conditions

Reaction Steps

A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), 6-valerolactam (120 mg, 1.21 mmol), K3PO4 (430 mg, 2.03 mmol), briefly evacuated and backfilled with argon. N,N′-Dimethylethylenediamine (11 μL, 0.10 mmol, 10 mol %), 3-iodobenzylamine (134 μL, 1.01 mmol), and toluene (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 100° C. for 18 h. The resulting pale yellow suspension was allowed to reach room temperature, and then 30% aq ammonia (1 mL) and water (10 mL) were added. The biphasic mixture was extracted with CH2Cl2 (3×15 mL). The combined organic phases were dried (Na2SO4), concentrated, and the residue was purified by flash chromatography on silica gel (2×15 cm; CH2Cl2 (saturated with 30% aq ammonia)-CH2Cl2—MeOH 10:10:1; 15 mL fractions). Fractions 14-19 provided 199 mg (96% yield) of the product as a pale yellow oil.

Provenance & Evidence