Acetic Acid → N-(4-cyanophenyl)-N-(5,6,7,8-tetrahydro-1-naphthyl)acetamide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of N-(5,6,7,8-tetrahydro-1-naphthyl)acetamide (23 g, 0.12 mole) in DMF (120 ml) was added 80% NaH (3.9 g, 0.13 mole) portionwise over a 45 minute period and the mixture was stirred until hydrogen evolution had ceased as monitored by bubbler. 4-Fluorobenzo-nitrile nitrile (18 g, 0.15 mole) (Aldrich) was added, and the solution stirred at 90° C. under nitrogen for 3 hours. The reaction mixture was acidified with acetic acid, diluted with water (500 ml), and extracted with methylene chloride (2×500 ml). The combined extracts were washed with water (100 ml), dried (MgSO4), and concentrated in vacuo. The residue in a small volume of methylene chloride was applied to a silica gel column and eluted with ethyl acetate:hexane (1:3) to give N-(4-cyanophenyl)-N-(5,6,7,8-tetrahydro-1-naphthyl)acetamide (13.4 g). 1H NMR (CDCl3, 200 MHz) δ: 1.55-1.85 (m, 4H, CH2's), 1.96 (s, 3H, CH3), 2.10-2.32 (m, 1H, ArCH2), 2.47-2.66 (m, 1H, ArCH2), 2.76-2.88 (m, 2H, ArCH2), 7.06 (dd, J=7, 2 Hz, 1H, Ar), 7.13-7.29 (m, 2H, Ar), 7.40 (d, J=9 Hz, 2H, Ar), 7.55 (d, J=9 Hz, 2H, Ar). Anal. Calculated for C19H18N2O: C, 77.16; H, 6.34; N, 9.47. Found: C, 77.08; H, 6.12; N, 9.51.

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