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General Procedure for preparation of compounds 6a-k: To a mixture of the amine 4 (1 mmol) in ethyl acetate (15 ml) was added triethylamine (1.1 mmol) and DMF (3 drops) followed by the addition of the benzoyl chloride (1.1 mmol) in ethyl acetate (5 ml) at room temperature. The reaction mixture was warmed to 50°C and stirred for 4 hours. The organic extract was washed with saturated aqueous NaCl solution, dried (Mg2SO4, filtered and evaporated. Flash chromatography on silica gel using mixture of ethyl acetate and hexane as eluent, provided the target compound 6a-k as solid. Preparation of unavailable benzoyl chlorides for preparation of compounds 6f, 6g, 6h, 6i, 6j, 6k, Excess of thionyl chloride was added to corresponding benzoic acid and the resulting mixture was stirred at 50oC for 4 hours. Thionyl chloride was removed by distillation under reduced pressure and residue dried under vacuum
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4), filtered and evaporated. Flash chromatography on silica gel using mixture of ethyl acetate and hexane as eluent, provided the target compound 6a-k as solid. Preparation of unavailable benzoyl chlorides (for preparation of compounds 6f, 6g, 6h, 6i, 6j, 6k): Excess of thionyl chloride was added to corresponding benzoic acid and the resulting mixture was stirred at 50oC for 4 hours. Thionyl chloride was removed by distillation under reduced pressure and residue dried under vacuum.
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42149196308
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Selected data for compound 6i: Yield, 65, m.p. 99-102°C. 1H NMR (500 MHz, MeOD, 7.33 (d, 2H, J, 7.0 Hz, 7.22 (m, 3H, 7.13 (m, 2H, 6.79 (d, 1H, J, 8.0 Hz, 5.98 (dd, 2H, J, 3.0 Hz, 2J, 1.0 Hz, 4.44 (dt, 1H, J, 10.5 Hz, 2J, 4.0 Hz, 3.99 (m, 1H, 3.14 (dd, 1H, J, 11.5 Hz, 2J, 2.5 Hz, 3.05 (m, 2H, 2.69 (dd, 1H, J, 12.5 Hz, 2J, 8.0 Hz, 2.62 (dd, 1H, J, 11.0 Hz, 2J, 3.0 Hz, 2.19 (m, 2H, 2.09 (dd, 1H, J, 24.5 Hz, 2J, 13.0 Hz, 1.96 (m, 1H, 1.81 (m, 1H, 1.74 (m, 1H, 1.66 (m, 1H, 1.57 (m, 2H, 1.49 (dd, 1H, J, 13.5 Hz, 2J, 3.5 Hz, 1.43 (t, 2H, J, 7.0 Hz, 2J, 3.5 Hz, 1.37 (m, 1H, 1.26 (s, 9H, 13C NMR 100 MHz, MeOD, 176.2; 167.1; 149.3; 140.6; 136.5; 133.2; 132.9; 130.5; 129.9; 129.3; 127.2; 125.7; 71.6; 71.4; 60
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13C NMR (100 MHz, MeOD): 176.2; 167.1; 149.3; 140.6; 136.5; 133.2; 132.9; 130.5; 129.9; 129.3; 127.2; 125.7; 71.6; 71.4; 60.3; 60.2; 57.2; 51.9; 37.7; 36.1; 35.2; 32.2; 31.7; 28.8; 27.6; 27.3; 21.9.
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1242271971
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