Piperocaine

Piperocaine
Clinical data
ATC code	none;
Identifiers
	IUPAC name 3-(2-Methylpiperidin-1-yl)propyl benzoate;
CAS Number	136-82-3 ;
PubChem CID	10782;
ChemSpider	10326 ;
UNII	F66XUI6GZL;
ChEMBL	ChEMBL127865 ;
CompTox Dashboard (EPA)	DTXSID8048315 ;
ECHA InfoCard	100.004.784
Chemical and physical data
Formula	C16H23NO2
Molar mass	261.365 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1CCCCN1CCCOC(C2=CC=CC=C2)=O;
	InChI InChI=1S/C16H23NO2/c1-14-8-5-6-11-17(14)12-7-13-19-16(18)15-9-3-2-4-10-15/h2-4,9-10,14H,5-8,11-13H2,1H3 ; Key:YQKAVWCGQQXBGW-UHFFFAOYSA-N ;
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Piperocaine is a local anesthetic drug developed in the 1920s and used as its hydrochloride salt for infiltration and nerve blocks.

Synthesis

Alkylation between 3-chloropropyl benzoate [942-95-0] (1) and Pipicoline [109-05-7] (2) provides piperocaine (3).

^ McElvain, S. M. (1927). "PIPERIDINE DERIVATIVES IV. SUBSTITUTED PIPERIDINE-ALKYL BENZOATES AND PARA-AMINOBENZOATES". Journal of the American Chemical Society 49 (11): 2835–2840. doi:10.1021/ja01410a030.
^ Samuel M Mcelvain, U.S. patent 1,784,903 (1930).