A kind of synthetic method of n-(3-cyanopropyl) formamide compound
A formamide and cyanopropyl technology, which is used in the synthesis of N-formamide compounds, can solve the problems of expensive transition metal catalysts, poor compatibility of substrate functional groups, harsh reaction conditions, etc. Simple, accessible results
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Embodiment 1
[0012]
[0013] Add compound 1a (0.2mmol, 32mg) and acetonitrile (CH 3 CN, 1mL), then add 2,2,6,6-tetramethyl-1-piperidine tetrafluoroborate (T + BF 4 - , 0.3mmol, 73mg), TBN (90wt%, 0.6mmol, 79μL) and activated Molecular sieve (100mg) (activated Molecular sieve is coming Molecular sieves were dried in a muffle furnace at 500°C for 5 hours). The reaction was stirred at room temperature under an air atmosphere for 1 hour, then 10 mL of saturated sodium chloride solution was added to quench the reaction, extracted with ethyl acetate (10 mL×3), the organic phases were combined, and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=2:1, v / v) to obtain the yellow liquid product N-(3-cyanopropyl)-N-phenylcarboxamide 2a (23mg, 61%). The characterization data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 )δ: 1.91-1.98(m, 2H), 2.38(t, J=7.2Hz, 2H), 3.95(t, J=7.2Hz, 2H), 7.18-7.20(m, 2H)...
Embodiment 2
[0015] Add compound 1a (0.2mmol, 32mg) and acetone (1mL) in a 15mL reaction flask, then add 2,2,6,6-tetramethyl-1-oxypiperidine tetrafluoroborate (T + BF 4 - , 0.3mmol, 73mg), TBN (90wt%, 0.6mmol, 79μL) and activated Molecular sieves (100 mg). The reaction was stirred at room temperature under an air atmosphere for 1 hour, then 10 mL of saturated sodium chloride solution was added to quench the reaction, extracted with ethyl acetate (10 mL×3), the organic phases were combined, and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=2:1, v / v) to obtain the yellow liquid product N-(3-cyanopropyl)-N-phenylcarboxamide 2a (19mg, 51%).
Embodiment 3
[0017] Add compound 1a (0.2mmol, 32mg) and tetrahydrofuran (1mL) in a 15mL reaction flask, then add 2,2,6,6-tetramethyl-1-oxypiperidine tetrafluoroborate (T + BF 4 - , 0.3mmol, 73mg), TBN (90wt%, 0.6mmol, 79μL) and activated Molecular sieves (100 mg). The reaction was stirred at room temperature under an air atmosphere for 1 hour, then 10 mL of saturated sodium chloride solution was added to quench the reaction, extracted with ethyl acetate (10 mL×3), the organic phases were combined, and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=2:1, v / v) to obtain the yellow liquid product N-(3-cyanopropyl)-N-phenylcarboxamide 2a (15mg, 40%).
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