1-Naphthalen-2-yl-ethylamine

Synthesis

1201-74-7

98-88-4

114459-78-8

3976-23-6

3082-62-0

1201-74-7

GENERAL METHODS: The N-acylation of racemic 1-(naphthalen-2-yl)ethanamine, 1,2 and 3 was carried out in cyclohexane in the presence or absence of TIPS-β-CD using benzoyl chloride as the acylating reagent and triethylamine as the base. First, racemic 1-(naphthalen-2-yl)ethylamine, 1,2 and 3 (6.0 × 10^-4 mmol) were mixed with 6-O-methylsilylated β-CD in cyclohexane (600 μL) and stirred for 1 h to reach complexation equilibrium. Subsequently, 6-O-methylsilylated β-CD, triethylamine (6.0 x 10^-4 mmol) and benzoyl chloride 4a-j were added at 10 °C. The reaction mixture continued to be stirred for 6 h at 10 °C. Upon completion of the reaction, it was analyzed using chiral high-performance liquid chromatography (HPLC) on a Diacel Chiralcel OD-H column (250 mm × 4.6 mm I.D.), with the eluent being hexane/2-propanol (80:20 or 95:5), at a flow rate of 0.5 or 1.5 mL/min, and with the UV detection wavelength at 254 nm.The reaction was analyzed by HPLC in the absence and presence of the presence and in the presence of TIPS-β-CD (3.0 × 10^-3 mmol), the N-acylation reaction of 1-(naphthalen-2-yl)ethylamine, 1,2 and 3 (6.0 × 10^-4 mmol) with benzoyl chloride 4a-j (3.3 × 10^-4 mmol) in cyclohexane (600 μL) and triethylamine (6.0 × 10^-4 mmol) yielded the products, and the results are displayed in Figures 1 and 2 and S18-26, respectively.

References