Quaternary Salts of Triethylenediamine - Journal of Medicinal

May 1, 2002 - Robert Bruce Moffett. J. Med. Chem. , 1964, 7 (4), pp 450–453. DOI: 10.1021/jm00334a011. Publication Date: July 1964. ACS Legacy Archi...
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Quaternary Salts of 7'rieth?rlenediarnine

t-

R - N D -R'

.x,-

NO.

1 P ,'3 1

ii

,

8 9 IO

@

COW---..OH

11

&

OH H

--

lIl3r

1"

OH &'H.--.H -..OH

1 :i

OH 14 1-I

I3r

. IiiO

TiJllP

1 .i 16 17 IX

J Slhe ~ diqiiiiternarj- salts :ire h s e d 011 l l i v The j-ields of the ~nonoi~uatern;iry salts are based o n the d k y l halide used (1:si . T ~ I I of trithylenedianiine used. The yields of the acid additions salts are based on the c~orrespondingmonoquaternary salt bases. l'nless otherwise specified the yields are based on materials iyhose decomposition points are not more than 2' below those of the anal>-zed Water was det,ermined by the Karl Fisher method. c The product which crystallized from the reaction mixture had 1 t l . p . samples. I ti%--]7,5' and an infrared spectrum prac?icallg identical with that of the rerrystallized (andytiml) sample. The large differcwe in melting points niay be due to different degrees of hydration or to diniorphic forms. See I~kperimentalsection for specific prep:irathi o f this conipound. e Analysis by Huffman Microanalytical Laboratories. 1 This prciduct \ v a s preripitated frorri the reac-tion rriisturc: ti\. The decuniposition point, was not strxrp. There \\its some sintering from 220". !' Tfiv the addition of 400 ml. of methyl ethyl ketone. 'f

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Syateiiiatically iiaiurii l,~-die~ahicycloi2.2.2lucranP. f 2 1 .4. \V. Ilofiiiann, Jahrcsbuv. Portsthi.. Chcnr.. (IS. S W . (LoIi~lonl.9, 153 (18,591. il

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