Chemical Properties
Colorless or yellow liquidcrystalline
Uses
1-(1-Naphthyl)ethylamine is used in the enzymic resolution of amines. A chirality modifier.
General Description
The adsorption of 1-(1-naphthyl)ethylamine on platinum surfaces has been characterized by reflection-absorption infrared spectroscopy and temperature-programmed desorption both under ultrahigh vacuum and
in situ from liquid solutions.
Synthesis
General procedure for the synthesis of 1-naphthylethylamine from 1-naphthylethanone: The corresponding ketone (10 mmol, specifically 1.14 g of 1a, 0.98 g of 1b, 1.48 g of 1c, 1.46 g of 1d, 1.46 g of 1e, 1.32 g of 1f, 1.20 g of 1g, 1.70 g of 1h, 1.70 g of 1i) was mixed with hydroxylamine hydrochloride ( 15 mmol, 1.04 g), ammonium formate (60 mmol, 3.78 g) and zinc powder (30 mmol, 1.96 g) in methanol (30 mL) and the reaction was stirred under reflux conditions. After completion of the reaction, the reaction mixture was filtered through Celite. The filtrate was subjected to vacuum rotary evaporation to remove the solvent. The residue was treated with concentrated hydrochloric acid followed by the addition of 4 mL of HCl solution and 30 mL of water and extracted with ether (2 x 20 mL) to remove organic impurities. The aqueous phase was adjusted to pH=10 with ammonia and extracted with dichloromethane (4 x 25 mL). The organic phases were combined, washed with saturated saline, dried over anhydrous sodium sulfate, and finally the solvent was removed in vacuum to obtain the target product 1-naphthylethylamine.
References
[1] Tetrahedron Letters, 2011, vol. 52, # 12, p. 1310 - 1312
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 21, p. 6197 - 6208
[3] Patent: WO2008/58235, 2008, A2. Location in patent: Page/Page column 23-24
[4] Synthetic Communications, 2011, vol. 41, # 3, p. 341 - 346
[5] Molecules, 2014, vol. 19, # 12, p. 21386 - 21397
