Configurational Effect in N-Alkylation of Diastereomeric 2-Aminocyclohexanol.

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The N-alkylation of DL-trans-and DL-cis-2-aminocyclohexanols was effected with alkylating agents in the presence of potassium carbonate. When lower alkylating agents were used, the trans form gave N-dialkyl derivatives, while the cis form gave only N-monoalkyl derivatives. The use of higher alkylating agents led both forms to N-monoalkyl derivatives. The resistance of the cis form to dialkylation in the presence of the lower alkylating agents was presumably due to a hydrogen bond between the hydroxyl and the amino groups in the cis relationship. This assumption may be supported by an analogous phenomenon which was already found in the Schotten-Baumann benzoylation of diasteromeric 2, 2'-dihydroxydicyclohexylamine.2, 15)

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