SCH-5472
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| Formula | C19H23NO |
| Molar mass | 281.399 g·mol−1 |
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SCH-5472.[1] is a stimulant drug[2] developed by Schering-Plough in the 1950s.[1]
Synthesis
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Potassium amide was made from the reaction of potassium metal with liquid ammonia. The coupling between the carbanion created from diphenylmethane [101-81-5] (1) and ethyl 2-furoate [614-99-3] [1335-40-6] (2) gives 2-furyl benzhydryl ketone, CID:63950182 (3). This was reacted with concentrated liquid ammonia in methanol solvent in an autoclave. The product of this step was 2-benzhydrylpyridin-3-ol, CID:125491889 (4). Reduction of the pyridine gave 2-(diphenylmethyl)piperidin-3-ol, CID:209477 (5).
See also
[edit]References
[edit]- ^ a b US patent 2997478, Walter LA, Sperber N, "Oxygenated Piperidines and Process for their Manufacture", issued 1961-08-22, assigned to Schering
- ^ Nodine JH, Bodi T, Slap J, Levy HA, Siegler PE (December 1960). "Preliminary trial of a new stimulant SCH 5472 in ambulatory patients with depression, exhaustion, or hypersomnia syndrome". Antibiotic Medicine & Clinical Therapy. 7: 771–6. PMID 13729397.
- ^ Walter, L., Springer, C., Kenney, J., Galen, S., & Sperber, N. (1968). Derivatives of 3-Piperidinol as Central Stimulants. Journal of Medicinal Chemistry, 11(4), 792–796. https://doi.org/10.1021/jm00310a612
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