3,3-Diphenylcyclobutanamine

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]

3,3-Diphenylcyclobutanamine
Clinical data
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
IUPAC name
  • 3,3-diphenylcyclobutan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC16H17N
Molar mass223.319 g·mol−1
3D model (JSmol)
SMILES
  • c1ccc(cc1)C3(c2ccccc2)CC(N)C3
InChI
  • InChI=1S/C16H17N/c17-15-11-16(12-15,13-7-3-1-4-8-13)14-9-5-2-6-10-14/h1-10,15H,11-12,17H2 Y
  • Key:IABBZBVTZRKDFW-UHFFFAOYSA-N Y
  (verify)

Synthesis

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

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

Preparation of Diphenylketene

See also

References
  1. 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 JW, Dabek RA, Welzel KC (1972). "Transannular neophyl rearrangement". The Journal of Organic Chemistry. 37 (3): 425–430. doi:10.1021/jo00968a022.
  3. Michejda CJ, Comnick RW (1975). "Acetolysis of 3,3-disubstituted cyclobutyl tosylates". The Journal of Organic Chemistry. 40 (8): 1046–1050. doi:10.1021/jo00896a010.
  4. Taylor EC, McKillop A, Hawks GH (1972). Michejda CJ, von Riesen DD, Comnick RW, Baumgarten HE (eds.). "DIPHENYLKETENE [Ethenone, diphenyl-]". Organic Syntheses. 52: 36. doi:10.15227/orgsyn.052.0036.
  5. Das, Madhurima; Weissenfluh, Amber; Ly, Nam; Trudell, Mark L. (2020). "Synthesis of Simple 3,3-Diarylazetidines fromN-Boc-3-arylazetidinols Using Friedel–Crafts Arylation Conditions". The Journal of Organic Chemistry. 85 (12): 8209–8213. doi:10.1021/acs.joc.0c00454. ISSN 0022-3263. PMID 32449343. S2CID 218873364.
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