3,3-Diphenylcyclobutanamine

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3,3-Diphenylcyclobutanamine
3,3-Diphenylcyclobutanamine.png
Systematic (IUPAC) name
3,3-diphenylcyclobutan-1-amine
Clinical data
Legal status Uncontrolled
Identifiers
ATC code None
PubChem CID 47486
ChemSpider 43204 YesY
Chemical data
Formula C16H17N 
Mol. mass 223.31 g/mol
 YesY (what is this?)  (verify)

3,3,-Diphenylcyclobutanamine is a psychostimulant drug which was originally prepared as an antidepressant in the late 1970s.[1] It appears to inhibit the reuptake of serotonin, norepinephrine, and dopamine, and may also induce their release as well.[1] The N-methyl and N,N-dimethyl analogues of the compound are also known and are more potent.[1] All three agents produce locomotor stimulation in animal studies, with the tertiary amine being the strongest.[1]

Synthesis[edit]

A number of methods were tried in order to construct the strained four-carbon ring. A synthesis of 3,3-diphenylcyclobutanone appeared in the literature.[2] The ketone was prepared in low yield by the reaction of diphenylketene with 2 equiv of diazomethane.[3] The latter synthesis, although low yielding, was used and the desired amines were prepared from 3,3-diphenylcyclobutanone.

Diphenylketene[edit]

Diphenylketene is produced by the elimination of hydrogen chloride from diphenylacetyl chloride in the presence of triethylamine.[4]

Preparation of Diphenylketene

See also[edit]

References[edit]

  1. ^ a b c d Carnmalm B, Rämsby S, Renyi AL, Ross SB, Ogren SO (January 1978). "Antidepressant agents. 9. 3,3-Diphenylcyclobutylamines, a new class of central stimulants". Journal of Medicinal Chemistry 21 (1): 78–82. doi:10.1021/jm00199a014. PMID 22757. 
  2. ^ Wilt, J. W.; Dabek, R. A.; Welzel, K. C. (1972). "Transannular neophyl rearrangement". The Journal of Organic Chemistry 37 (3): 425. doi:10.1021/jo00968a022.  edit
  3. ^ Michejda, C. J.; Comnick, R. W. (1975). "Acetolysis of 3,3-disubstituted cyclobutyl tosylates". The Journal of Organic Chemistry 40 (8): 1046. doi:10.1021/jo00896a010.  edit
  4. ^ Submitted by Edward C. Taylor Alexander McKillop, and George H. Hawks. Checked by C. J. Michejda, D. D. von Riesen, R. W. Comnick, and Henry E. Baumgarten. (1972). "DIPHENYLKETENE [Ethenone, diphenyl-]". Organic Syntheses 52: 36. doi:10.15227/orgsyn.052.0036.  edit