The Reaction of 1-Dimethylamino-2-chloropropane with Diphenylacetonitrile. The Structure of Amidone

Abstract

Vol. 69 temperature was maintained below 45°until the exothermic reaction stopped. Excess dimethyl sulfate was decomposed by heating to 90°for two hours. The upper layer of the reaction mixture was washed with water, dried, and fractionally distilled at reduced pressure to give a 60% yield of the ether. Calculated for CnHieO: C, 80.44; H, 9.82. Found: C, 80.37; H, 9.98. Cyclohexyl Methyl Ether.17-Anisóle (750 g., 7 moles) was hydrogenated in the presence of 75 g. of nickel-onkieselguhr catalyst at 180°to give 600 g. of ether, 76%.Cyclopropyl Methyl Ether.-Glycerol was brominated, in approximately 18 mole runs, to glycerol a,7-dibromohydrin, in 60% yields, following the procedure of Braun.18 The dibroinohydrin (10.8 moles, 2347.5 g.) was treated with 1449 g. (11.5 moles) of dimethyl sulfate according to Krantz and co-workers.19 A mixture of 212 g. (2 moles)

Some Derivatives of Amidone

“…138-140°and was identical with the product according to May and Mosettig (10). 4.5-Diphenyl-S-dimethylamino-4-pentanol (X). The reaction between /3-dimethylaminobutyrophenone (VIII) and benzylmagnesium chloride was carried out as above, but at 0°.…”

Selective methodologies for the synthesis of biologically active piperidinic compounds

“…In 1947, it was noticed that β‐chloroamine hydrochlorides of type D and E undergo a rearrangement under basic conditions 57–61. The products obtained were α‐chloroamines of type F and these compounds were believed to occur through a cyclic aziridinium intermediate of type G (Scheme , equation 1).…”

Opioids: 3.4 Opioids with Clinical Relevance

“…Hoechst), 1941;Schultz et al,1947;Howe and Sletzinger, 1949;Solmssen and Wenis,1948;Larsen et al,1948, Howe et al (Merck & Co), 1953Zaugg (Abott), 1961): Hoechst), 1941;Schultz et al,1947;Howe and Sletzinger, 1949;Solmssen and Wenis,1948;Larsen et al,1948, Howe et al (Merck & Co), 1953Zaugg (Abott), 1961):…”