{"title":"2-氨基甲基-5-叔丁基苯酚的合成","authors":"G. Fukata, T. Kanai, S. Mataka*","doi":"10.15017/7876","DOIUrl":null,"url":null,"abstract":"Mannich-type aminomethylation of m-ten-butylphenol (1) with a variety of secondary amines and formalin was carried out in ethanol at 70-80°C for 2 h. The reaction with amines such as pyrrolidine, piperidine, N-methylpiperazine, and N-benzylpiperazine gave the expected products, 2-pyrrolidinomethyl(2b), 2-piperidinomethyl(2d), 2-(N-methylpiperazino)methyl(2e), and 2-(N-benzylpiperazino)-methyl-5-te11-butylphenol (2 f) in high yields. In the reaction with piperazine, the desired compound, 2-(piperazinomethyl)-5-ten-butylphenol (2g) was not fonned and N,N'-bis(2-hy<toxy4-tert-butylbenzyl)piperazine (3) and bis[N,N'-di (2-hy<toxy-4-ten-butylbenzyl)]piperazinomethane (4) were produced in 52% and 38% yields, respectively. 2-(Dimethylamino)methyl-5-te11-butylphenol (2a) was obtained, albeit in a poor yield, when aqueous 10 % potassium hydroxide solution was a.tIed to the reaction mixture with dimethylammonium chloride to generate the free amine. Addition ofthe base was effective in the Mannich conoonsation with morpholine, giving the OOsired 2(morpholino)methyl-5-ten-butylphenol (2c) in a moderate yield Without the base, the reaction did not occur.","PeriodicalId":22886,"journal":{"name":"The reports of Institute of Advanced Material Study Kyushu University","volume":"61 6","pages":"125-129"},"PeriodicalIF":0.0000,"publicationDate":"1997-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of 2-Aminomethyl-5-tert-butylphenols\",\"authors\":\"G. Fukata, T. Kanai, S. Mataka*\",\"doi\":\"10.15017/7876\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Mannich-type aminomethylation of m-ten-butylphenol (1) with a variety of secondary amines and formalin was carried out in ethanol at 70-80°C for 2 h. The reaction with amines such as pyrrolidine, piperidine, N-methylpiperazine, and N-benzylpiperazine gave the expected products, 2-pyrrolidinomethyl(2b), 2-piperidinomethyl(2d), 2-(N-methylpiperazino)methyl(2e), and 2-(N-benzylpiperazino)-methyl-5-te11-butylphenol (2 f) in high yields. In the reaction with piperazine, the desired compound, 2-(piperazinomethyl)-5-ten-butylphenol (2g) was not fonned and N,N'-bis(2-hy<toxy4-tert-butylbenzyl)piperazine (3) and bis[N,N'-di (2-hy<toxy-4-ten-butylbenzyl)]piperazinomethane (4) were produced in 52% and 38% yields, respectively. 2-(Dimethylamino)methyl-5-te11-butylphenol (2a) was obtained, albeit in a poor yield, when aqueous 10 % potassium hydroxide solution was a.tIed to the reaction mixture with dimethylammonium chloride to generate the free amine. Addition ofthe base was effective in the Mannich conoonsation with morpholine, giving the OOsired 2(morpholino)methyl-5-ten-butylphenol (2c) in a moderate yield Without the base, the reaction did not occur.\",\"PeriodicalId\":22886,\"journal\":{\"name\":\"The reports of Institute of Advanced Material Study Kyushu University\",\"volume\":\"61 6\",\"pages\":\"125-129\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"1997-12-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"The reports of Institute of Advanced Material Study Kyushu University\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.15017/7876\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"The reports of Institute of Advanced Material Study Kyushu University","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.15017/7876","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Mannich-type aminomethylation of m-ten-butylphenol (1) with a variety of secondary amines and formalin was carried out in ethanol at 70-80°C for 2 h. The reaction with amines such as pyrrolidine, piperidine, N-methylpiperazine, and N-benzylpiperazine gave the expected products, 2-pyrrolidinomethyl(2b), 2-piperidinomethyl(2d), 2-(N-methylpiperazino)methyl(2e), and 2-(N-benzylpiperazino)-methyl-5-te11-butylphenol (2 f) in high yields. In the reaction with piperazine, the desired compound, 2-(piperazinomethyl)-5-ten-butylphenol (2g) was not fonned and N,N'-bis(2-hy
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