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]
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Formula | C16H17N |
Molar mass | 223.319 g·mol−1 |
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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 is produced by the elimination of hydrogen chloride from diphenylacetyl chloride in the presence of triethylamine.[4]