N-METHYLCYCLODODECYLAMINE synthesis

Yield:40221-53-2 2.6 g

Reaction Conditions:

Stage #1: cyclododecanone;methylamine in methanol; for 2 h;Reflux;
Stage #2: with lithium aluminium tetrahydride in tetrahydrofuran at 0 - 20;

Steps:

N-Methylcyclodedecanamine

Cyclododecanone (3.0 gm,16.5 mmol) and 2M methylamine in tetrahydrofuran(9.9 mL, 19.8 mmol) were dissolved in anhydrous tetrahydrofuran(40 mL). The mixture was cooled to 0 °C andthen treated with lithium aluminum hydride (1M in tetrahydrofuran,8.2 mL, 8.2 mmol). The reaction mixture wasallowed to come up to room temperature and then stirredovernight. The reaction was quenched by dropwise additionof saturated ammonium chloride and then extracted withdichloromethane. The organic layer was washed with waterand brine, dried over anhydrous magnesium sulfate andconcentrated on a rotary evaporator. The crude product(2.60 gm, 80%) was obtained as a white solid and was usedin the subsequent reaction without further purification.ESIMS m/z (pos) 198.3 (100%) [M+ H]+.

References:

Childers, Wayne E.;Gordon, John;Hewlett, Elizabeth;Skorski, Tomasz;Sliwinski, Tomasz;Sullivan-Reed, Katherine;Toma, Monika;Tulin, Alexei [Medicinal Chemistry Research,2020]