Aminonitrile reduced to a 2 - Aminopropane -Wizard X , Hive Serious Chemistry


dormouse (Member) 04-19-00 06:14 No 122777	Aminonitrile reduced to a 2 - Aminopropane -Wizard X	Bookmark
	the Hive BB Serious Chemistry Forum Aminonitrile reduced to a 2 - Aminopropane profile \| register \| preferences \| faq \| search next newest topic \| next oldest topic Author Topic: Aminonitrile reduced to a 2 - Aminopropane Wizard X Moderator posted 12-07-98 07:38 PM -------------------------------------------------------------------------------- A great man once said , " I have a dream " I thought I would share this synthesis challenge with you all. The problem here is two fold. Ph = C6H5- PhCH2CHO == ( 1 ) NH3 == ( 2 ) HCN ==>> PhCH2CHCN === ( 3 ) H3O+ ==>> PhCH2CHCOOH \ NH2 \ NH2 The challenge here is to reduce the -CN group to a -CH3 group , with the least synthesis steps possible. I do not want hydrolyses of the CN to a COOH , and then follow the steps I suggested in converting the COOH group to a CH3 group in the thread, " MDA form Coffee ". I have experimented with one reaction ( two steps ) , but found too many side reactions and by-products. All input appreciated. Wizard X Moderator posted 12-07-98 07:45 PM -------------------------------------------------------------------------------- PhCH2CHO is Phenyl acetaldehyde PhCH2CH(NH2)CN is aminonitrile PhCH2CH(NH2)COOH is DL - Phenylalanine Osmium Member posted 12-08-98 02:32 PM -------------------------------------------------------------------------------- R-CN can be reduced to the nitrile in one step, eg with Pd/C and a terpene (limonene, which acts as reducing agent). Lit: Kindler, Luehrs, Chem. Ber. 1966, 99, 227 and Liebigs Ann. Chem. 1967, 707, 26 (apparently both in German) H2 can be used, too, but higher temp is required. Wizard X Moderator posted 12-17-98 08:47 PM -------------------------------------------------------------------------------- Osmium, thanks for the input. I will investigate. Have already reduced the -CN to a -CH2NH2 group, but the cleaverage of the primary -NH2 to a -CH3 group is a challenge. Piglet Member posted 12-18-98 03:36 AM -------------------------------------------------------------------------------- O: You just answered a question I had forgotten to ask for YEARS! I have read in several places that Limonine is 'watched', or at least connected with clandestine synthesis. I had no idea why, until now. Always nice to learn something newe! Piglet Beagle Member posted 12-18-98 09:21 AM -------------------------------------------------------------------------------- Piglet: Do you mean this limonine: What good is that? Beagle Member posted 12-18-98 09:26 AM -------------------------------------------------------------------------------- Oh, maybe I should have read the entire thread B4 I asked that question. Seems awful wierd to use this terpene as a reducing agent. Ammonium formate or cyclohexene I could see being useful for CTH, but this? I was thinking that it might be watched because of potential use in THC syntheses. All times are CT (US) next newest topic \| next oldest topic Administrative Options: Close Topic \| Archive/Move \| Delete Topic Hop to: Select a Forum or ArchiveList of Forums:General DiscussionAcquisition DiscourseChemistry DiscourseMethods DiscourseNovel DiscourseCrystal MethSerious Chemistry ForumThe Hive CouchSerious Tryptamine DiscourseAdmin Chill-out TentList of Archives:Couch ArchivesClassics!Law and OrderThe litter box.misc. PEAs Contact Us \| the Hive Powered by: Ultimate Bulletin Board, Version 5.39a © Infopop Corporation (formerly Madrona Park, Inc.), 1998 - 1999.