N-(hept-4-yl) benzo [d] [1, 3] dioxole-5-methanamide and synthetic method thereof

Abstract

The invention discloses a synthetic method of N-(hept-4-yl) benzo [d] [1, 3] dioxole-5-methanamide. The step comprises the 3 steps of: mixing 4-heptanone and an ethanol solution of ammonia for reaction catalyzed by an organo-metallic catalyst M, then adding sodium borohydride for reduction to prepare 4-heptylamine; synthesizing piperonyloyl chloride, as well as subjecting the synthesized 4-heptylamine with the synthesized piperonyloyl chloride to an amidation reaction so as to prepare N-(hept-4-yl) benzo [d] [1, 3] dioxole-5-methanamide. The synthetic method of the invention employs an organic metal-NaBH4 system to conduct a reductive amination reaction to a ketone compound so as to synthesize the important intermediate 4-heptylamine, and the generated primary amine no longer reacts with ketone, also the selectivity and yield are both high. In the method, the raw materials adopted are cheap and easily available, the solvent used can be recycled and utilized again, the production cost is low, and the reaction conditions are mild. With simple and convenient operation as well as little "three wastes", the method provided in the invention is suitable for industrial production.

Description

technical field [0001] The present invention relates to N-(hept-4-yl)benzo[d][1,3]dioxol-5-carboxamide and its synthesis method. Background technique [0002] The full name of food flavor enhancer is food flavor enhancer, also known as umami agent, which refers to a class of substances that have a delicious taste and can be used to supplement or enhance the flavor of food. Adding umami to food can enhance some flavor characteristics of food, such as persistence, taste, crispness, mildness, and richness. Currently available food flavor enhancers mainly include amino acid flavor enhancers, nucleotide flavor enhancers, organic acid flavor enhancers and compound flavor enhancers; the most important flavor enhancer is L-glucose Monosodium glutamate (MSG), commonly known as monosodium glutamate. However, MSG has been found to cause adverse reactions in certain populations, and small amounts of naturally occurring substances such as inosinic acid or guanylic acid can enhance th...

AI Technical Summary

Problems solved by technology

(J. Chem. Soc. Perkin Trans. I 1984, 717; 1994, 1; 2000, 503) (Tetrahedron Lett. 2002, 43, 3150; 2001, 42, 1245) (Synthesis 2000, 789) Reduction of these predecessors Amination work has a lot of good results for the synthesis of tertiary amines, but poor results for the synthesis of primary and secondary amines due to overalkylation reactions

Because the generated primary amine will undergo further reductive alkylation reaction with the carbonyl group still present in the reaction system to generate various numbers of secondary and tertiary amines, which makes these methods unsuitable for the synthesis of primary amines

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