Benproperine

Benproperine (INN) is a cough suppressant.^[1] It has been marketed in multiple countries in Central America and Europe, as the phosphate or pamoate salts in either tablet, dragée, or syrup form. Trade names include Blascorid in Italy and Sweden, Pectipront and Tussafug in Germany, and Pirexyl in Scandinavia. The recommended dosage for adults is 25 to 50 mg two to four times daily, and for children 25 mg once or twice daily. Adverse effects include dry mouth, dizziness, fatigue, and heartburn.^[2]

Benproperine

Clinical data
Trade names	Blascorid, Pectipront, Pirexyl, Tussafug
AHFS/Drugs.com	International Drug Names
ATC code	R05DB02 (WHO)
Identifiers
IUPAC name (RS)-1-[2-(2-Benzylphenoxy)-1-methylethyl]piperidine
CAS Number	2156-27-6 Y 19428-14-9 (phosphate salt)
PubChem CID	2326
ChemSpider	2236 Y
UNII	3AA6IZ48YK
KEGG	D07512 Y
ChEMBL	ChEMBL2105910
CompTox Dashboard (EPA)	DTXSID10862853
Chemical and physical data
Formula	C21H27NO
Molar mass	309.453 g·mol−1
3D model (JSmol)	Interactive image
SMILES O(c1ccccc1Cc2ccccc2)CC(N3CCCCC3)C
InChI InChI=1S/C21H27NO/c1-18(22-14-8-3-9-15-22)17-23-21-13-7-6-12-20(21)16-19-10-4-2-5-11-19/h2,4-7,10-13,18H,3,8-9,14-17H2,1H3 Y Key:JTUQXGZRVLWBCR-UHFFFAOYSA-N Y
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Synthesis

The base-catalyzed ether formation between 2-benzylphenol (1) and 1,2-dichloropropane (2) gives 1-benzyl-2-(2-chloropropoxy)benzene (3).^[3][4][5][6] Displacement of the remaining halogen with piperidine completes the synthesis of benproperine (4).

Synthesis of benproperine