Reactions of β-substituted amines—III: Complete product study of the reactions of 3-chloro-1-ethylpiperidine and 2-chloromethyl-1-ethylpyrrolidine with hydroxide ion☆

Add time:09/01/2019    Source:sciencedirect.com

A complete product study of the reaction of 3-chloro-1-ethylpiperidine (1) in aqueous sodium-hydroxide showed the formation of three bis-(β-aminoethers), 2,2′-bis-(N-ethyl-2-pyrrolidinomethyl) ether (6), 3-(N′-ethyl-2′-pyrrolidinomethoxy)-N-ethylpiperidine (7) and 3,3′-bis-N-ethyl-3-piperidinyl ether (8) in addition to the two previously reported products. The structures of these three ethers are demonstrated and their formation is shown to be consistent with the previously suggested mechanism1 of the reaction. Reactions of 2-chloromethyl-1-ethylpyrrolidine (2) are shown to proceed by the same mechanistic pathways with the formation of the same products. Reaction of 1 or 2 with two other nucleophiles, methoxide and ethoxide are also examined.

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