SCH-5472

SCH-5472
Identifiers
	IUPAC name 2-benzhydryl-1-methyl-piperidin-3-ol;
CAS Number	20068-90-0 (phenylsuccinate);
PubChem CID	209634;
ChemSpider	181634 ;
UNII	2D4V6AWP8N;
CompTox Dashboard (EPA)	DTXSID50942087 ;
Chemical and physical data
Formula	C19H23NO
Molar mass	281.399 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES OC(CCCN1C)C1C(C2=CC=CC=C2)C3=CC=CC=C3;
	InChI 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 ; Key:DQNBDZSLMWHFTB-UHFFFAOYSA-N ;
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SCH-5472.^[1] is a stimulant drug^[2] developed by Schering-Plough in the 1950s.^[1]

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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).

[1]
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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[US2997478-1] [1]
US patent 2997478, Walter LA, Sperber N, "Oxygenated Piperidines and Process for their Manufacture", issued 1961-08-22, assigned to Schering

[2] [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] [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

[1]

[2]

[3]

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SCH-5472

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Synthesis

See also

References

Identifiers

IUPAC name 2-benzhydryl-1-methyl-piperidin-3-ol
CAS Number	20068-90-0^Y (phenylsuccinate)
PubChem CID	209634
ChemSpider	181634^N
UNII	2D4V6AWP8N
CompTox Dashboard (EPA)	DTXSID50942087
Chemical and physical data
Formula	C₁₉H₂₃NO
Molar mass	281.399 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES OC(CCCN1C)C1C(C2=CC=CC=C2)C3=CC=CC=C3
InChI 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
^NY (what is this?) (verify)