SCH-5472
{{Short description|Stimulant drug}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 451224999
| IUPAC_name = 2-benzhydryl-1-methyl-piperidin-3-ol
| image = SCH-5472.svg
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| CAS_supplemental = (phenylsuccinate)
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 20068-90-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2D4V6AWP8N
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| PubChem = 209634
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 181634
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = DQNBDZSLMWHFTB-UHFFFAOYSA-N
| C=19 | H=23 | N=1 | O=1
| smiles = OC(CCCN1C)C1C(C2=CC=CC=C2)C3=CC=CC=C3
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SCH-5472. is a stimulant drug{{cite journal | vauthors = Nodine JH, Bodi T, Slap J, Levy HA, Siegler PE | title = Preliminary trial of a new stimulant SCH 5472 in ambulatory patients with depression, exhaustion, or hypersomnia syndrome | journal = Antibiotic Medicine & Clinical Therapy | volume = 7 | pages = 771–6 | date = December 1960 | pmid = 13729397 }} developed by Schering-Plough in the 1950s.{{ cite patent | country = US | status = patent | number = 2997478 | inventor = Walter LA, Sperber N | gdate = 1961-08-22 | assign1 = Schering | title = Oxygenated Piperidines and Process for their Manufacture }}
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, [https://pubchem.ncbi.nlm.nih.gov/compound/63950182 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, [https://pubchem.ncbi.nlm.nih.gov/compound/125491889 CID:125491889] (4). Reduction of the pyridine gave 2-(diphenylmethyl)piperidin-3-ol, [https://pubchem.ncbi.nlm.nih.gov/compound/209477 CID:209477] (5).
See also
References
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