SCH-5472

SCH-5472.^[1] is a stimulant drug^[2] developed by Schering-Plough in the 1950s.^[1]

SCH-5472

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)

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

• AL-1095
• Desoxypipradrol
• Difemetorex