dormouse (Member)
04-19-00 06:14
No 122777
      Aminonitrile reduced to a 2 - Aminopropane -Wizard X  Bookmark   


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Author  Topic:   Aminonitrile reduced to a 2 - Aminopropane 
Wizard X
Moderator   posted 12-07-98 07:38 PM          
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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          
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PhCH2CHO is Phenyl acetaldehyde
PhCH2CH(NH2)CN is aminonitrile

PhCH2CH(NH2)COOH is DL - Phenylalanine


Osmium
Member   posted 12-08-98 02:32 PM          
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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          
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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          
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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          
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Piglet: Do you mean this limonine:
 
What good is that?


Beagle
Member   posted 12-18-98 09:26 AM          
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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.


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