Benzhydrylamine → HCID 10729452, compound

Participants

Reaction Steps

A 100-mL round-bottomed flask containing a stir bar was charged with Na2SO4 (8.0 g) and CH2Cl2 (40 mL). Trimethylacetaldehyde (8) (7.65 mL, 52 mmol, 1.3 equiv) and aminodiphenylmethane (9) (6.89 mL, 40 mmol, 1.0 equiv) were added sequentially via syringe while stirring. The flask was capped with a plastic stopper, and the mixture was stirred at room temperature. The mixture became cloudy after 5 min. After stirring for 1 h, the mixture was decanted into a 200 mL round-bottomed flask, rinsing with CH2Cl2 (4×5 mL), and concentrated to 8-10 mL using a rotary evaporator. The flask was then maintained at 1 torr for 10 min. The resulting pale yellow solid was taken up in CH2Cl2 (50 mL), transferred to a 250-mL separatory funnel, and washed with NaHCO3 (50 mL). The organic layer was dried over Na2SO4, filtered through a medium porosity fitted disk funnel into a 200-mL round-bottomed flask, and concentrated in vacuo (30 torr→1 torr) to provide a pale yellow oil that solidified to a white solid within 5 min at 1 torr. The solid was broken up into approximately 1-cm diameter pieces using a spatula, and was maintained at 1 torr for another 15 min to provide N-(2,2 dimethylpropylidene) diphenylmethanamine (2a) as a white solid in approximately 98% 1H-NMR purity. The product was used in the next step without further purification. Yield: 9.79 g (38.9 mmol, 97%).

Provenance & Evidence