Tert-Butylamine → HCID 89422940, compound

Participants

Reaction Steps

To a solution of 1-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)butan-1-one (2.94 g, 13.5 mmol) in CH2Cl2 (14 mL) was added 2-methylpropan-2-amine (5.7 mL, 54.2 mmol, 4.0 eq). The mixture was cooled to 0° C. before TiCl4 (1.0M in CH2Cl2, 8.8 mL, 8.8 mmol, 0.65 eq) was added via syringe pump over 30 min. The reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was quenched with saturated aqueous NaHCO3 (15 mL) then extracted by CH2Cl2 (5×25 mL). The combined organic layers were dried over Na2SO4 then concentrated to give a crude product which was carried over to next step without further purification. LC-MS 273.1 [M+H]+, RT 0.65 min. (1 min Method).

Provenance & Evidence