3,3-Diphenylcyclobutanamine

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	64895-45-0 Y
PubChem CID	47486
ChemSpider	43204 Y
UNII	CN43PDA78X
Chemical and physical data
Formula	C16H17N
Molar mass	223.319 g·mol−1
3D model (JSmol)	Interactive image
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
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3,3,-Diphenylcyclobutanamine is a psychostimulant drug which was originally prepared as an antidepressant in the late 1970s. It appears to inhibit the reuptake of serotonin, norepinephrine, and dopamine, and may also induce their release as well. The N-methyl and N,N-dimethyl analogues of the compound are also known and are more potent. All three agents produce locomotor stimulation in animal studies, with the tertiary amine being the strongest.

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. The ketone was prepared in low yield by the reaction of diphenylketene with 2 equiv of diazomethane. 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.

Preparation of Diphenylketene

See also

• β-Phenylmethamphetamine
• Fezolamine
• Azetidine ring variation: