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Phenacaine

Names
IUPAC name (1E)-N,N′-Bis(4-ethoxyphenyl)ethanimidamide
Identifiers
CAS Number	101-93-9
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL127123
ChemSpider	7307
PubChem CID	7588
UNII	V3M4D317W8
CompTox Dashboard (EPA)	DTXSID0046062
InChI InChI=1S/C18H22N2O2/c1-4-21-17-10-6-15(7-11-17)19-14(3)20-16-8-12-18(13-9-16)22-5-2/h6-13H,4-5H2,1-3H3,(H,19,20)
SMILES O(c1ccc(cc1)N\C(=N\c2ccc(OCC)cc2)C)CC
Properties
Chemical formula	C18H22N2O2
Molar mass	298.386 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Phenacaine, also known as holocaine, is a local anesthetic. It is approved for ophthalmic use.

Synthesis

The synthesis of phenacaine begins with the condensation of p-phenetidine (1) with triethyl orthoacetate (2) to afford the imino ether (a Pinner salt, 3). Reaction of that intermediate with a second equivalent of the aniline results (4) in a net displacement of ethanol, probably by an addition-elimination scheme, producing the amidine, phenacaine (5).

In the patented synthesis, phenacetin was used as precursor. Treatment with phosphorus trichloride (PCl₃) gave the enol chloride, and reaction of this intermediate with p-phenetidine then completed the synthesis of phenacaine.

References

1. "Holocaine Hydrochloride".
2. Merck Index, 1985
3. DeWolfe, Robert H. (1962). "Reactions of Aromatic Amines with Aliphatic Ortho Esters. A Convenient Synthesis of Alkyl N-Arylimidic Esters". Journal of Organic Chemistry. 27 (2): 490–493. doi:10.1021/jo01049a036.
4. DE 79868, Ernst Taeuber, issued 1894 

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