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| Abstract |
Mannich-type aminomethylation of m-tert-butylphenol (1) with a variety of secondary amines and formalin was carried out in ethanol at 70-80℃ for 2h. The reaction with amines such as pyrrolidine, piper...idine, N-methylpiperazine, and N-benzylpiperazine gave the expected products, 2-pyrrolidino-methyl-(2b), 2-piperidinomethyl-(2d), 2-(N-methylpiperazino)methyl-(2e), and 2-(N-benzyl-piperazino)-methyl-5-tert-butylphenol (2f) in high yields. In the reaction with piperazine, the desired compound, 2-(piperazinomethyl)5-tert-butylphenol (2g) was not formed and N,N'-bis(2-hydroxy-4-tert-butylbenzyl)piperazine (3) and bis [N,N'-di (2-hydroxy-4-tert-butylbenzyl)]piperazinomethane (4) were produced in 52% and 38% yields, respectively. 2-(Dimethylamino)methyl-5-tert-butylphenol (2a) was obtained, albeit in a poor yield, when aqueous 10% potassium hydroxide solution was added to the reaction mixture with dimethylammonium chloride to generate the free amine. Addition of the base was effective in the Mannich condensation with morpholine, giving the desired 2-(morpholino)methyl-5-tert-butylphenol (2c) in a moderate yield. Without the base, the reaction did not occur.show more
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