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Interpretation Of The Noesy: Nuclear Overhauser Effect

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Interpretation of the NOESY: (Nuclear Overhauser Effect) spectrum of 1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)azepan-2-one (3a) is as follows.
Strong coupling interaction of protons of 2nd and 4th position in 1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)azepan-2-one (3a), was not so strongly observed in COSY because it involves long range coupling i.e. protons attached between 2nd and 4th carbon atom. Hence, we studied NOESY to know the spacial interaction between these two protons.
Thus, the NOESY of compound 1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl) azepan-2-one (3a) is predicted as shown in Fig.5. In the NOESY of compound 1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)azepan-2-one (3a) we got additional cross peak which was not observed …show more content…
IR (KBr): ʋ= 3292.63 (N-H), 2931.93 (ArH), 1716.06 (C=O) cm-1; 1H NMR (400 MHz, CDCl3): δ=1.30 (d, J=6.40 Hz, 3H), 1.37-1.39 (m, 1H), 1.55-1.56 (m, 3H), 1.72 (d, J=0.80 Hz, 2H), 1.83 (d, J=7.60 Hz, 3H), 2.03 (dd, J=6.40, 14.40 Hz, 1H), 2.20 (s, 3H), 2.60-2.63 (m, 3H), 3.01-3.03 (m, 2H), 3.47-3.48 (m, 1H), 6.01 (dd, J=6.40, 11.60 Hz, 1H), 6.65 (d, J=6.80 Hz, 1H), 6.73 (s, 1H),6.85 (d, J=8.00 Hz, 1H) ppm. 13C NMR (400 MHz, DMSO-d6): δ=20.20,21.83, 23.13, 29.14, 34.69, 36.83, 43.61, 46.41, 50.41, 114.10, 118.93, 124.19, 126.56, 127.94, 128.61,144.72, 175.19 ppm; MS (70 eV) m/z (%): 273.1 (M+, 100.00). HPLC Purity=99.52%.

cis-[2-methyl-6-(trifluoromethoxy)-1,2,3,4-tetrahydroquinolin-4-yl]azepan-2-one (3g)
Elution from silica using 10% ethyl acetate in hexane afforded the title compound (3g) as a white solid. 1H NMR (300 MHz, CDCl3): 1.22 (d, J=6.3 Hz, 3H), 1.51-1.31 (m, 1 H), 1.86-1.53 (m, 6 H), 2.04-1.97 (m, 1 H), 2.68-2.64 (m, 2 H), 3.17-3.02 (m, 2 H), 3.57-3.51 (m, 1 H), 3.80 (s, 1 H), 6.04-5.98 (m, 1 H), 6.46 (d, J=8.7 Hz, 1 H), 6.73 (s, 1 H), 6.88-6.84 (m, 1 H) ppm. 13C NMR (75 MHz, CDCl3) =22.14, 29.96, 34.36, 37.52, 44.63, 47.10, 51.01, 114.92, 115.57, 118.95, 120.34, 121.12, 122.34, 125.72, 140.68, 145.22, 176.71; MS (70 eV) m/z (%): 343.1(M+, 97.49). HPLC Purity=99.08%.

cis-1-(1,2,3,4-tetrahydro-2-methyl-6-phenoxyquinolin-4-yl)azepan-2-one …show more content…
IR (KBr): ʋ= 3310.18(N-H), 2925.53(ArH), 1628.65(C=O) cm-1; 1H NMR(300 MHz, DMSO-d6): δ=1.79 (s, 3H), 1.91-1.93 (m, 1H), 2.26-2.31 (m, 1H), 2.34-2.36 (m, 5H), 3.00 (d, J=9.57 Hz, 2H), 3.20-3.23 (m, 2H), 3.53 (s, 2H), 5.10 (s, 1H), 5.31-5.33 (m, 1H), 6.48-6.51 (m, 2H), 6.93-6.96 (m, 2H), 7.08 (d, J=7.35 Hz, 1H), 7.31-7.39 (m, 2H) ppm.13C NMR (400 MHz, DMSO-d6): δ=21.89, 22.64, 28.14, 29.31, 36.36, 37.18, 41.95, 46.36, 48.17, 114.81, 115.41, 117.29, 117.62, 118.26, 119.14, 122.97, 129.16, 129.79, 140.16, 140.70, 156.82, 174.05 ppm. MS (70 eV) m/z (%): 385.2(M+1). HPLC

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