Cyrax
(Hive Bee)
10-09-02 03:58
No 366431
      Diampromide
(Rated as: excellent)
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Diampromide was develloped at the American Cyanamid Company, by some chemists who modified the methadone molecule a bit.

Preliminary clinical results indicate that the potency of diampromide lies between that of meperidine and morphine.


Synthesis:

A benzene solution of N-methylphenethylamine(1) and 2-bromopropionanilide(2) was heated under reflux to give 2-(N-methylphenethylamino)-propionanilide in 81 % yield (M.P.: 65- 67 C).  The reduction of 2-(N-methylphenethylamino)-propionanilide with LiAlH4in THF afforded 80 % of N2-methyl-N2-phenethyl-N1-phenyl-1,2-propanediamine (B.P.: 138 - 144 C / 0.2 mm Hg).  When N2-methyl-N2-phenethyl-N1-phenyl-1,2-propanediamine was acylated with propionic anhydride N-[2-(methyl-phenethylamino)-propyl]-propionanilide was obtained in 83 % yield (B.P.: 174 - 178 C / 0.5 mm Hg).  The sulphate salt crystallized from EtOH - Et2O in 85 % yield (M.P.: 110 - 111 C).

Precursors:
(1) J. Chem. Soc. (1910) p 2253
(2) Ber. (1892) vol 25 p 2919
 
Ref.: JACS (1959) vol 81 p 1518 - 1519


A comparison between diampromide, 2,3-seco-fentanyl and fentanyl can be found at:
http://www.ch.ic.ac.uk/ectoc/echet98/pub/028/index.htm
Diampromide seems to be 167 times less potent than fentanyl.  Hence, I estimate that the dose would be 4 - 8 mg.
 
 
 
 
    Bwiti
(PVC-Analog Taste-Tester)
10-09-02 04:18
No 366435
      Sweet! I wonder if Na-borohydride/nickel boride ...  Bookmark   

  Sweet! I wonder if Na-borohydride/nickel boride could replace the LAH? If diampromide is more euphoric and less sedating than prodine or analogs, then it would be worth making. Peace!cool

Love my country, fear my government.
 
 
 
 
    Cyrax
(Hive Bee)
10-09-02 10:26
No 366541
      refs.
(Rated as: excellent)
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I don't know if the P-2 catalyst (normally used to reduce alkenes) can be used to reduce amides ...

But I have refs. for coreactants that can be used with NaBH4 to reduce amides:
* Tetrahedron Lett. (1969) p 4555
* Tetrahedron Lett. (1976) p 219
* J.Org. Chem. (1977) vol 42 p 2082
* J.Org. Chem. (1981) vol 46 p 2579
* Synthesis (1987) p 1128
* Chem. Lett. (1990) p 251 
Mabey Ni2B is one of them.  I know it will work with  BF3 or Me3SiCl as a coreagent.
BF3 + NaBH4 will in situ generate borane (cfr. J. Org. Chem. (1973) vol 38 p 912). 
And trichlorosilane even reduces amides without NaBH4.  Ref.: Chem. Lett. (1972) p 989.

What looks promessing, is that all kinds amides can be reduced with Na in 1-propanol.  However, the article is somewhat difficult to obtain: Chem. Ind. (London) (1990) p 547.

Bwiti, I would say: up to the library smile