Mistryukov, E. A. published the artcileSynthesis and steric structure of some 1-methyl-4-phenyl-4-piperidinols, COA of Formula: C7H16ClNO2, the publication is Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1961), 623-6, database is CAplus.
cf. CA 52, 20159b. PhLi from 17 g. Li treated in Et2O with 127.6 g. 1-methylperhydro-4-pyrindone gave, after refluxing 4 h. and treating with aqueous HCl, followed by NaOH, 44% 1-methyl-4-phenylperhydro-4-pyrindole (I), b0.3 136-46°, m. 45.5-6.5° (HCl salt m. 221-2°), along with a small amount of a base, C23H29NO, m. 71-2°; the mother liquors gave a base, m. 4850° (picrate decomposed at 199-200°; propionate HCl salt m. 206-7°), whose structure was not determined I formed a picrate, m. 157-7.5°. PhLi and 1-methyldecahydro-4-quinolone gave 63.7% isomeric alcs. in 62:24:14 ratio: α-form of 1-methyl-4-phenyldecahydro-4-quinolol, m. 126.5-7°; β-form, m. 112-13° (HCl salt m. 216-19°); and γ-form, m. 148-50°. Heating (CCMe2OH)2 with p-MeC6H4SO3H in the presence of pyrogallol at 100°/100 mm. 1 h. gave H2O and CO2 and a residue of 2,5-dimethyl-1,5-hexadien-3-yne, b40 46-9°, and 2,5-dimethyl-5-hexen-3-yn-2-ol, b13 64-7°. Treatment of 2,5-dimethyl-1,4-hexadien-3-one and its MeOH adducts (crude mixture, Nazarov and Bukhmutskaya, CA 42, 7733e) with 39% aqueous MeNH2 2 days at room temperature gave, after treatment with H2O and aqueous HCl, followed by NaOH, 40% 1,2,2,5-tetramethyl-4-piperidone, b15 90-3°, n20D 1.4620 (HCl salt m. 195.5°; picrate m. 180-80.5°). This and PhLi gave only 1 isomer of 1,2,2,5-tetramethyl-4-phenyl-4-piperidinol, m. 81-2°; HCl salt m. 201° (hydrate m. 152-3°). This piperidinol probably had equatorial Ph and Me groups at C-5. Only I showed evidence of internal H-bonding in the IR spectrum.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya published new progress about 6249-56-5. 6249-56-5 belongs to chlorides-buliding-blocks, auxiliary class Phase Transfer Catalyst,Inhibitor,Natural product, name is 3-Carboxy-N,N,N-trimethylpropan-1-aminium chloride, and the molecular formula is C7H16ClNO2, COA of Formula: C7H16ClNO2.
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