Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 13729-77-6, is researched, Molecular C6H12ClNO, about Synthesis of some N-substituted 2-methyl- and 3-methyl-4-piperidones, the main research direction is PIPERIDONES.Category: pyridine-derivatives.
cf. CA 60, 15825b. 1,2-Dimethyl-4-piperidone-MeI (I) heated with Me2C(NH2)CCH (Ia) in H2O 3.5 hrs. at 80° in a sealed tube and kept 2 days at room temperature gave a low yield of 1-(1,1-dimethyl-2-propynyl)-2-methyl-4-piperidone (II), m. 50-2°. I treated with ice-cold KOH gave 42% Me2NCH2CH2COCH:-CHMe, b2 46-7°, n19.5D 1.4593, which with MeI in Me2CO gave the methiodide, a solid, which with Ia, finally at 80°, gave 72% II. To 287 g. AlCl3 in CHCl3 was added 227 g. ClCH2CH2COCl followed at -20° by MeCH:CH2 passed in for 2.5 hrs., after which an aqueous treatment gave mixed chlorides, b8 94-5°, which with Ia in aqueous K2CO3, finally 10 hrs. at 80°, gave some II. Keeping CH2:CHCO2Me with MeCH(NH2)CH2CO2Et 2 days gave 69.5% MeO2CCH2CH2NHCHMeCH2CO2Et, b6 127-30°, n17D 1.4410, which with Na in liquid NH3, followed by an aqueous treatment, gave after acidification and heating to expel CO2, treatment with KOH and extraction with CHCl3, 43% 2-methyl-4-piperidone, isolated as N-benzoyl derivative, m. 88°, and as HCl salt. The HCl salt and tosyl chloride in pyridine 1 day gave 1-(p-tolylsulfonyl)-2-methyl-4-piperidone, m. 80-1°. Similarly was prepared 1-(p-tolylsulfonyl)-3-methyl-4-piperidone (III), m. 104-5°. Heating MeO2CCH:CH2 with MeCH(NHMe)CH2CO2Et 12 hrs. at 52° gave 53% MeO2CCH2CH2NMeCHMeCH2CO2Et, b6 129-30°, n17D 1.4420, which with Na in liquid NH3, then with aqueous HCl, gave 76% 1,2-dimethyl-4-piperidone, b7 55-7°, n18D 1.4592. III heated 8 hrs. with KOH and cyclohexylamine gave traces of N-cyclohexyl-3-methyl-4-piperidone; Me3CNH2 with KOH also gave traces of the N-tert-butyl derivative
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