SCH-5472
Identifiers
  • 2-benzhydryl-1-methyl-piperidin-3-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H23NO
Molar mass281.399 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
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SCH-5472.[1] is a stimulant drug[2] developed by Schering-Plough in the 1950s.[1]

Synthesis

Synthesis:[3]

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. ^ a b US patent 2997478, Walter LA, Sperber N, "Oxygenated Piperidines and Process for their Manufacture", issued 1961-08-22, assigned to Schering 
  2. ^ 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.
  3. ^ 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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