Original scientific paper

Necrosamine Series. II.* Synthesis of Racemic 4,5-Diaminoeicosane and of 2-Methyl-3,4-diaminononadecane

P. Alaupović ; Department of Chemistry, Medical Faculty, University of Zagreb andDepartment of Biochemistry, Institute »Ruder Boskovic«, Zagreb, Croatia, Yugoslavia
M- Proštenik ; Department of Chemistry, Medical Faculty, University of Zagreb andDepartment of Biochemistry, Institute »Ruder Boskovic«, Zagreb, Croatia, Yugoslavia

Abstract

Racemic 4,5-diaminoeicosane (I) and 2-methyl-3,4-diaminononadecane (II) were obtained by reaction of dibenzyl sodiotetradecylmalonate (III) with N-phthaloyl-DL-norvalinoyl chloride (IVa) and N-phthaloyl-DL-valinoyl chloride (IVb). Following compounds were prepared: Dibenzyl tetradecylmalonate (III), m . p . 42-42.5°; N-phthaloyl-DL-norvaline, m. p. 102-103°; N-phthaloyl-DL-norvalinoyl chloride (IVa), b . p. 158° /1 mm; 4-phthalimido-5-eicosanone (Vla), m. p. 38-38.5°; 4-(o-carboxybenzamido)-5- eicosanone (VIIa), m. p. 111-112°; 4-amino-5-eicosanone hydrobromide (VIIIa), m. p. 95-96°; 4-amino-5-eicosane oxime (IXa), m. p. 114-115°;
4,5-diaminoeicosane dihydrochloride (Xa), m. p. 265-267°; 4,5 - diacetylaminoeicosane (Xla), m. p . 122-123°; 2-methyl-3-phthalimido- 4-nonadecanone (VIb), m. p. 52-53°; 2-methyl-3-(o-carboxybenzamido-)4-nonadecanone (VIIb), m. p . 118-119°; 2-methyl-3- amino-4-nonadecanone hydrobromide (VIIIb), m. p. 127-128° ; 2-methyl-3-amino-4-nonadecane oxime (IXb), m. p. 108-108.5°;2 - methyl - 3,4 - diaminononadecane dihydrochloride (Xb), m. p.225-226°; 2 - methyl - 3,4 - diacetylaminononadecane (XIb) , m. p. 136--138°. The synthesis of (I) and (II) represents at the same time a general method for the preparation of aliphatic a-diamines. The application of this procedure to some stereochemical questions is discussed.

Keywords

Hrčak ID:

246848

URI

https://hrcak.srce.hr/246848

Publication date:

7.11.1956.

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