Hello there,
Diphenylethylenediamine is generally synthesiszed by corey's method which is well known (Org. Synth.; Coll. Vol., 9, p. 387), but i'm unable able to perform the liquid ammonia/lithium reduction step due to shortage of facility in my lab. hence, I have been trying to synthesize Diphenylethylenediamine using benzaldehyde and ammonium acetate (ref. Tetrahedron: Asymmetry, 25(4), 381-386; 2014; Organic & Biomolecular Chemistry, 10(9), 1877-1882; 2012), the simpler version.
In the described two step process, i was able to prepare till the first step, where i could the see formation of white solid as per the literature. But i've been facing problem in the second step, hydrolysis in 70% sulfuric acid and subsequent neutralization. i have tried 4-5 times but failed. can any one help me with the process or suggest any other method to synthesize which i can follow in my humble lab?
Dear Sameer,
You may use the procedure published in Org. Synth. 1999, 76, 23
DOI: 10.15227/orgsyn.076.0023: in the first step, you react benzaldehyde with ammonia and to produce the imine and in the second step you react the imine with Zn/trimethylsilyl chloride in aceonitrile; see steps A and B in the following link:
http://www.orgsyn.org/demo.aspx?prep=v76p0023
Hoping this will be helpful,
Rafik
mannich base produce from two compounds of secondary amine with aldehyde .... but in most of papers we found SH , OH react with aldehyde and ketone , which one is the right ?? or ( R)2N with ketone and aldehyde is mannich reaction ??which one from these (( 3 types ) act mannich reaction?
dear @Rafik Karaman
thank you for your suggestion. here in the method i could see there is a formation of secondary amine rather than free amine which i need, as i intend to synthesize noyori catalyst ( ref: http://www.orgsyn.org/demo.aspx?prep=v82p0010). hence i need a free amine
dear Nagham Aljamali
i would need some more detail regarding your question. especially what exactly is your target.
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