19690-13-2Relevant articles and documents
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Liska,Tadepalli
, p. 2157,2159 (1968)
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Nucleophilic Addition of 2-, 3-, or 4-pyridine to the Aziridine, 7-Methyl-7-azabicycloheptane
Rees, David C
, p. 147 - 150 (2007/10/02)
The synthesis of trans-(+/-)-N-methyl-N-amino>cyclohexyl>-4-benzofuranacetamide dihydrochloride, 1 which is a 3-pyridyl derivative of the kappa opioid analgesic trans-(+/-)-N-methyl-N-benzofuran-4-acetamide monohydrochloride, 2 is described.The key intermediate is trans-(+/-)-N,N'-dimethyl-N--1,2-cyclohexanediamine, 9 which is formed by nucleophilic addition of 3-pyridine 6 to the aziridine, 7-methyl-7-azabicycloheptane, 4.During attempts to prepare the 2- or 4-isomeric pyridyl derivatives of 1 it was discovered that both 2- or 4-pyridine, 5 or 7 are converted to N-methyl-N,N-di- 11 and N-methyl-N,N-di 13 respectively by refluxing in toluene in the presence of ammonium chloride.The 3-isomer, 6 is unchanged after treatment under identical conditions.Careful control of the reaction conditions enabled the aziridine 4 to be ring opened with the pyridyl amines 5 or 7 to give the 1,2-diamines trans-(+/-)-N,N'-dimethyl-N--1,2-cyclohexanediamine, 8 or trans-(+/-)-N,N'-dimethyl-N--1,2-cyclohexane diamine 10 respectively.