YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
Azaquinolizine類の合成研究(第2報) : 1,3,4,6,7,8,9,9a-Octahydro-2H-pyrido[1,2-a]pyrazineの新合成法
山崎 高応永田 正典小川 清美野原 冨士夫
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1967 年 87 巻 6 号 p. 668-671

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Ethyl 2-piperidinecarboxylate was converted to the corresponding 1-cyanomethyl compound (I) by the strecker synthesis. I was reduced over Raney nickel catalyst at 130° at high pressure to 1, 3, 4, 6, 7, 8, 9, 9a-octahydro-2H-pyrido [1, 2-a] pyrazin-1 (9aH)-one (II). II was reduced to 1, 3, 4, 6, 7, 8, 9, 9a-octahydro-2H-pyrido [1, 2-a] pyrazine (III) with lithium aluminum hydride. The compound III was also prepared by another method according to the following process. 2-(Aminomethyl) pyridine was reacted with chloroacetyl chloride to give 2-(chloroacetamidomethyl) pyridine which was cyclized to the corresponding pyridinium salt (VI) by heating in alcoholic solution for 3 hr. The salt (VI) was then reduced over platinum oxide catalyst to 1, 3, 4, 6, 7, 8, 9, 9a, -octahydro-2H-pyrido [1, 2-a] pyrazin-3 (4H)-one (VII), which was reduced with lithium aluminium hydride to III.

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