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Synthesis of deuterium-labeled imipramine using acid-catalyzed exchange reaction

✍ Scribed by S. Baba; T. Furuta; Y. Sasaki; Y. Kasuya

Publisher
John Wiley and Sons
Year
1985
Tongue
French
Weight
367 KB
Volume
22
Category
Article
ISSN
0022-2135

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✦ Synopsis

h i g h i s o t o p i c p u r i t y u s i n g a c i d c a t a l y z e d hydrogen-deuterium exchange r e a c t i o n i s described. Deuterated imipramine l a b e l e d a t t h e p o s i t i o r s o f 2.4.6 and 8 [IP-d4(I)] was prepared d i r e c t l y by h e a t i n g imipramine i n 10% DC1-D20 a t 80" f o r 8hr. Imipramine l a b e l e d a t a l l o f t h e e i g h t a r o m a t i c p o s i t i o n s ( I P -d g ) was s y n t h e s i z e d f r o m i m i n o d i b e n z y l -1,2,3,4,6,7,8,9-d8 w h i c h was p r e p a r e d b y t r e a t i n g i m i n o d i b e n z y l (IDB) i n 37% DCl-D20 a t 160" f o r 24hr. And imipramine l a b e l e d a t t h e p o s it i o n s o f 1.3.7 and 9 [ I P -d 4 ( I I ) ] was o b t a i n e d b y "back-exchange'' o f IPdg u n d e r t h e p r o t i o c o n d i t i o n a c c o r d i n g t o t h e exchange p r o c e d u r e o f IP-d4( I).

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