N-(3-(Benzyloxy)phenethyl)naphthalen-1-aMine synthesis

Yield:295319-69-6 94%

Reaction Conditions:

in tetrahydrofuran;

Steps:

34.D D.

D. Naphthyl {2-[3-(phenylmethoxy)phenyl]ethyl}amine To a solution of N-naphthyl-2-[3-(phenylmethoxy)phenyl]acetamide (3.00 g, 8.16 mmol) in tetrahydrofuran (25 mL) under nitrogen was added a solution of 1.0 M borane-tetrahydrofuran complex in tetrahydrofuran (12.3 mL, 12.3 mmol) and heated to reflux for 5 hours. The reaction was quenched with a 5% hydrochloride solution. After stirring 30 minutes, the reaction was basified with a 10% sodium carbonate solution and extracted with CH₂Cl₂. The organic layer was dried over MgSO₄, filtered, and concentrated to provide the title compound (2.724 g, 94% yield): ¹H NMR (CDCl₃) 7.78 (d, 1H), 7.67 (d, 1H), 7.18-7.46 (m, 10H), 6.89 (m, 3H), 6.66 (d, 1H), 5.01 (s, 2H), 4.40 (br, 1H), 3.55 (t, 2H), 3.05 (t, 2H); ES-MS (m/z) 354 [M]⁺.

References:

US6436923,2002,B1