【摘要】 β-(3,4-二甲氧基)苯乙胺与甲醛及甲酸在封管中热至125°,生成N,N-二甲基衍生物.2-溴-1-(3,4-二甲氧基)苯乙烷与二乙胺或六氢吡啶缩合则成相应N,N-二乙基衍生物或N-六氢吡啶衍生物.在无水碳酸钠作用下,N-甲基-β-(3,4-二甲氧基)苯乙胺经氯化苄、2-溴-1-苯乙烷或2-溴-1-(3,4-二甲氧基)苯乙烷烷化,分别生成相应N-甲基-N-芳烷基-β-(3,4-二甲氧基)苯乙胺.β-(3,4-二甲氧基)苯乙胺经乙酸酐或苯乙酰氯酰化后,再以五氧化二磷环化,并以锌粉及盐酸还原,分别制成1-甲基及1-苄基-6,7-二甲氧基-1,2,3,4-四氢异喹啉.以上制成的化合物均可认为是镇痛药延胡索素乙的裂环化合物,并已进行药理试验.更多还原

【Abstract】 Tetrahydropalmatin (Ⅰ), a constituent isolated from Chinese plant Corydalis ambigus,is a potent analgesic. Several simpler compounds possessing analogous structural skeleton were synthesized in the present work.N, N-Dimethyl-β-(3,4-dimethoxy)-phenethylamine (Ⅱb) was prepared on treatment of β-(3,4-dimethoxy)-phenethylamine with formaldehyde and formic acid in a sealed tube at 125°. The corresponding N, N-diethyl compound (Ⅱc) was formed by condensation of β-(3,4-dimethoxy)-phenethyl bromide with diethylamine. Similar condensation with piperi-dine gave the piperidino compound (Ⅲ).In the presence of anhydrous sodium carbonate, N-methyl-β.(3,4-dimethoxy)-phene-thylamine condensed with benzyl chloride, β-phenethyl bromide or β-(3,4-dimethoxy)-phenethyl bromide in ethanolic media, forming the corresponding N-methyl-N-aryl-β-(3,4-dimethoxy)-phenethyl amines (Ⅳ, Ⅴ).Acylation of β-(3,4-dimethoxy)-phenethylamine with acetic anhydride or phenylacetyl chloride, followed by cyclisation of the amides by means of phosphorus pentoxide and reduction of the products with zinc dust in hydrochloric acid gave 1-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline and 1-benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(Ⅶa) respectively.Pharmacological tests of the compounds prepared are in progress, and will be published elsewhere.更多还原