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3-OXO-N-(3-PHENYL-PROPYL)-BUTYRAMIDE synthesis

2synthesis methods
-

Yield:112369-47-8 71%

Reaction Conditions:

with triethylamine in toluene at 80; for 3 h;

Steps:

61.1

1 Synthesis of 3-oxo-N-(3-phenylpropyl) butylamide: 3.00 g of (22.2 mmol) of 3-phenylpropylamine, 3.39 ml (40.3 mmol) of diketene and 3.37 g (33.3 mmol) of triethylamine were heated and stirred in 20 ml of toluene at 80° C. for 3 hours. After saturated aqueous sodium hydrogencarbonate solution was added, the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain the title compound. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=3/1) to obtain the title compound. Yield: 3.48 g (15.9 mmol) (71%) MS (ESI, m/z) 218 (M-H)- 1H-NMR (CDCl3): 1.86 (2H, quint), 2.26 (3H, s), 2.66 (2H, t), 3.30 (2H, q), 3.39 (2H, s), 6.96 (1H, br), 7.17-7.21 (3H, m), 7.26-7.31 (2H, m).

References:

US2004/9991,2004,A1 Location in patent:Page/Page column 28