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Short description : Stimulant drug
SCH-5472 Identifiers
2-benzhydryl-1-methyl-piperidin-3-ol
CAS Number PubChem CID ChemSpider UNII Chemical and physical data Formula C 19 H 23 N O Molar mass 281.399 g·mol−1 3D model (JSmol )
OC(CCCN1C)C1C(C2=CC=CC=C2)C3=CC=CC=C3
InChI=1S/C19H23NO/c1-20-14-8-13-17(21)19(20)18(15-9-4-2-5-10-15)16-11-6-3-7-12-16/h2-7,9-12,17-19,21H,8,13-14H2,1H3
N Key:DQNBDZSLMWHFTB-UHFFFAOYSA-N
N
N Y (what is this?) (verify)
SCH-5472 .[1] is a stimulant drug[2] developed by Schering-Plough in the 1950s.[1]
Synthesis
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
References
↑ 1.0 1.1 Walter LA, Sperber N, "Oxygenated Piperidines and Process for their Manufacture", US patent 2997478 , issued 1961-08-22, assigned to Schering
↑ "Preliminary trial of a new stimulant SCH 5472 in ambulatory patients with depression, exhaustion, or hypersomnia syndrome". Antibiotic Medicine & Clinical Therapy 7 : 771–6. December 1960. 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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Original source: https://en.wikipedia.org/wiki/SCH-5472. Read more