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    Process for the preparation of cyclopropylmethyl alkyl amines
    93.
    发明授权
    Process for the preparation of cyclopropylmethyl alkyl amines 失效
    环丙基甲基丙烯酸烷基酯的制备方法

    公开(公告)号：US3739025A

    公开(公告)日：1973-06-12

    申请号：US3739025D

    申请日：1970-08-28

    申请人： EXXON RESEARCH ENGINEERING CO

    发明人： SCHMIT G ,  NEWMAN N ,  LINDER J ,  MARAVETZ L

    IPC分类号： C07B61/00 ,  B01J23/00 ,  C01B7/09 ,  C07C17/087 ,  C07C67/00 ,  C07C209/00 ,  C07C209/08 ,  C07C209/22 ,  C07C209/26 ,  C07C209/48 ,  C07C209/52 ,  C07C211/17 ,  C07C211/25 ,  C07C85/12 ,  C07C87/34

    CPC分类号： C07C209/52 ,  C01B7/093 ,  C07C17/087 ,  C07C209/08 ,  C07C209/48 ,  C07C19/075

    摘要： THIS INVENTION RELATES TO A METHOD FOR PREPARING CYCLOPROPYLMETHYL ALKYL AMINES AND ALKYLCYCLOPROPYLMETHYL ALKYL AMINES. THE METHOD COMPRISES THE STEPS OF REACTING AN ALLYLIC CHLORIDE WITH HYDROGEN BROMIDE IN THE PRESENCE OF A FREE RADICAL CATALYST TO FORM THE ANTI-MARKOWNIKOFF PRODUCT 1-BROMO-3-CHLOROPROPANE WHICH CAN BE OPTIONALLY SUBSTITUTED WITH C1-C4 ALKYL GROUPS, CONTACTING THE REACTION PRODUCT OF STEP ((1) WITH A METAL CYANIDE TO FORM A GAMMA-CHLORINITRILE, REACTING THE GAMMA-CHLORONITRILE WITH AN ALKALI METAL HYDROXIDE TO YIELD CYCLOPROPYL OR AN ALKYLCYCLOPROPYL CYANIDE, REACTING THE CYCLOPROPYL CYANIDE OR ALKYLCYCLOPROPYL CYANIDE WITH ANN ALKYL AMINE AND HYDROGENN TO YIELD A CYCLOPROPYLMETHYL ALKYL AMINE OR AN ALKYLCYCLOPROPYLMETHYL ALKYL AMINE. IN ANOTHER ASPECT OF THIS INVENTION, THE CYCLOPROPYL OR ALKYLCYCLOPROPYL CYANIDE IS REACTED WITH HYDROGEN AND THE RESULTING CYCLOPROPYLMETHYL AMINE OR ALKYLCYCLOPROPYLMETHYL AMINE IS THEN REACTED WITH EITHER A KETONE, ALDEHYDE, OR ALCOHOL AND HYDROGEN, OR WITH AN ALKYL HALIDE IN THE ABSENCE OF HYDROGEN, TO FORM EITHER CYCLOPROPYLMETHYL ALKYL AMINES OR C1-C4 ALKYLCYCLOPROPYLMETHYL ALKYL AMINES. IN STILL ANOTHER VARIATION OF THIS INVENTION, AN N-ALKYLIDENE CYCLOPRROPYLMETHYL AMINE, OR AN N-ALKYLIDENE ALKYLCYCLOPROPYLMETHYL AMINE, PREPARED BY REACTING A CYCLOPROPYLMETHYLAMINE OR AN ALKYLCYCLOPROPYLMETHYL AMINE WITH AN ALDEHYDE OR KETONE, CAN BE HYDROGENATED TO FORM THE CYCLOPROPYL METHYL ALKYL AMINES OR ALKYLCYCLOPROPYLMETHYL ALKYL AMINES. THE FORMATION OF CYCLOPROPYLMETHYL ALKYL AMINES AND ALKYLCYCLOPROPYLMETHYL AMINES WITHOUT CONCURRENT HYDROGENOLYSIS OF THE CYCLOPROPANE RING HAS PROVEN TO BE QUITE UNEXPECTED AND IS THE RESULT OF THE CAREFUL CONDITIONS UNDER WHICH THE CYCLOPROPYL CYANIDE OR ALKYLCYCLOPROPY CYANIDE IS REACTED WITH THE VARIOUS REACTANNTS STATED HEREINABOVE.