Category: 17983-30-1

17983-30-1, name is 3-Oxocyclohexanecarbonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 3-Oxocyclohexanecarbonitrile

Example 2Conversion of 3-cyanocyclohexanone to 3-aminomethyl-1-cyclohexylamineThe apparatus used consisted of 8 tubular reactors connected in series. The dimensions of the first two tubes (C1-C2) were 1500¡Á6¡Á1 mm. The dimensions of the 6 further tubes (C3-C8) were 2000¡Á8¡Á1.5 mm. The first two reactors (C1-C2) were charged with 15.7 g of TiO2 extrudates with a diameter of 1.5 mm, the remaining 6 reactors each with approx. 85 g of a hydrogenation catalyst (Mn3O4 5-6.2%, Na2O 0-0.5%, H3PO4 2.8-3.8%, remainder Co+CoO) which had been reduced with hydrogen at 280 C. at a pressure of 1 bar for 24 hours.The temperature of the first two reactors C1-C2 was adjusted to 60 C. The temperature of reactors C3-C4 was 90 C., the temperature of reactors C5-C6 was 115 C. and the temperature of reactors C7-C8 was set to 130 C. Between reactors C2 and C3, hydrogen was fed into the reaction mixture under pressure. The operating pressure was 230 bar.23 g/h of a mixture of THF and 3-cyanocyclohexanone in a ratio of 1:1 together with 73 g/h of NH3 were pumped into the first reactor (C1), and 17 standard liters/h of hydrogen were also fed in upstream of reactor C3. The reaction output was decompressed through a regulating valve. In a downstream phase separator, hydrogen was then removed and ammonia was evaporated off.A total of 592 g of 3-cyanocyclohexanone were used. The crude output was distilled through a 60 cm column with random packing at <1 mbar. The product distilled over at 54 C. 433.7 g of 3-aminomethyl-1-cyclohexylamine were obtained as a mixture of cis/trans isomers with a purity of 99.5% (cis: 85.6, trans: 14.1; CT ratio: 86:14). The yield in the hydrogenation stage was 84% including the product content in the different fractions and 70.4% of pure product after the distillation.The mixture of the isomeric diamines was characterized by GC-MS, NMR and elemental analysis.13C-NMR (125 MHz, DMSO): 50.33 (cis-AMCHA), 48.57 (cis-AMCHA), 47.22 (trans-AMCHA), 45.35 (trans-AMCHA) 41.26 (cis-AMCHA), 40.43 (cis-AMCHA), 38.02 (trans-AMCHA), 36.88 (cis-AMCHA), 35.03 (trans-AMCHA), 34.53 (trans-AMCHA), 29.87 (cis-AMCHA), 29.44 (trans-AMCHA), 24.61 (cis-AMCHA), 19.66 (trans-AMCHA).In the GC-MS, by the method of 30m db35 MS 0.25 micrometer, start temperature 60 C., temperature ramp 5 C./min to 280 C. and bakeout at this temperature for 30 min, two main peaks were detected, retention times 19.07 min (85.6 area %) and 19.2 min (14.1 area %).The following fragment distributions were obtained (M+=128 corresponds to the particular molecular peak):Peak 1:m/z (%)=18(5), 27(5), 28(14), 29(7), 30(59), 39(9), 41(15), 42(13), 43(48), 44(17), 53(5), 54(12), 55(11), 56(100), 57(15), 58(9), 67(23), 68(11), 69(17), 70(18), 71(3), 77(4), 79(6), 80(3), 81(9), 82(28), 83(9), 85(4), 94(3), 96(8), 98(79), 99(36), 110(6), 111(19), 112(3)Peak 2:m/z (%)=18(4), 27(6), 28(14), 29(7), 30(61), 39(10), 41(16), 42(15), 43(45), 44(12), 53(6), 54(11), 55(11), 56(100), 57(32), 58(9), 67(20), 68(11), 69(20), 70(18), 71(3), 77(4), 79(7), 80(3), 81(9), 82(25), 83(14), 84(3), 85(3), 94(3), 96(10), 98(68), 99(22), 110(7), 111(41), 112(5)To determine the elemental analyses, an Elementar Vario EI III automatic analyzer was used.The elemental analysis gave_C=64.8 (expected: 65.6); N=22.1 (expected: 21.9); H=12.8 (expected: 12.6) g/100 g The synthetic route of 17983-30-1 has been constantly updated, and we look forward to future research findings. Reference:
Patent; BASF SE; US2011/124919; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 17983-30-1, name is 3-Oxocyclohexanecarbonitrile, A new synthetic method of this compound is introduced below., Safety of 3-Oxocyclohexanecarbonitrile

Under a nitrogen atmosphere, lithium aluminum hydride (92 mg, 2.44 mmol) was added to a solution of 1-cyanocyclohexan-3-one (100 mg, 0.812 mmol) in tetrahydrofuran (2 ml) at room temperature, and the resulting mixture was refluxed. After 5 hours, water, an aqueous sodium hydroxide solution and water were added in that order to the reaction solution, and the resulting mixture was filtered under reduced pressure. Thereafter, 1M-hydrochloric acid-diethyl ether (974 mul, 0.974 mmol) was added to the filtrate. The resulting mixture was concentrated under reduced pressure, and to an aqueous solution (4 ml) of the resulting residue were added potassium carbonate (202 mg, 1.46 mmol), ethoxycarbonylphthalimide (196 mg, 0.893 mmol) and acetonitrile (1 ml) at room temperature. After 21 hours, the reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) and purified again by a silica gel column chromatography (eluent: chloroform/ethyl acetate) to obtain cis-2-[(3-hydroxycyclohexyl)methyl]-1Hisoindole-1,3(2H)-dione (83.5 mg, 40%, cis : trans = 12 : 1).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Sumitomo Pharmaceuticals Company, Limited; EP1403255; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts