Chemistry:Dimefadane
Dimefadane is an analgesic agent with about the same activity as codeine, but without any of the GI side effects. Although it does not adhere to the classical morphine rule (structure includes a tertiary amine, phenyl ring and quaternary carbon), it is not known if this is opioidergic.{{Citation needed|date=December 2024} ips that can be compared to tametraline. Klaus Bøgesø used dimefadane as the harbinger to Indatraline.[citation needed]
Synthesis
Synthesis:[1][2] Cyclic Normethadone derivative:[3] Patents:[4]
The Friedel-Crafts reaction between cinnamic acid [140-10-3] (1) and benzene in the presence of a Lewis acid catalyst gives 3,3-diphenylpropionic acid [606-83-7] (2). The cyclization of this gives 3-phenyl-1-indanone [16618-72-7] (3). Heating with ammonium formate (Leuckart reaction) gives 3-phenyl-1-indanamine, PC22346445 (4). Although reduction of the oxime would also work, perhaps there is differences in the proficiency between the different methods. Heating with formaldehyde and formic acid (Eschweiler-Clark reaction) then produces dimefadane (5).
References
- ↑ "570. Compounds of potential pharmacological interest. Part IV. Aryl and alkyl derivatives of 1-aminoindane". Journal of the Chemical Society (Resumed): 2928. 1956. doi:10.1039/JR9560002928.
- ↑ "БИС (БЕТА-ХЛОРЭТИЛ) АМИНЫ БИЦИКЛИЧЕСКИХ СОЕДИНЕНИЙ. 7. ПРОИЗВОДНЫЕ ИНДАНА". Zhurnal Obshchei Khimii 34 (10): 3414. 1964.
- ↑ "139. Compounds of potential pharmacological interest. Part 1. Acyl derivatives of 1-amino-3-phenylindane". Journal of the Chemical Society (Resumed): 691. 1956. doi:10.1039/jr9560000691.
- ↑ Dr Helmer Richter, Dr Martin Schenck, DE951628 & DE946058 (1953 & 1956 both to Schering Ag).
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