Phenacaine

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−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Phenacaine, also known as holocaine,^[1] is a local anesthetic. It is approved for ophthalmic use.^[2]

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).

Synthesis:^[3]

In the patented synthesis,^[4] 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

^ "Holocaine Hydrochloride".
^ Merck Index, 1985
^ 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.
^ DE 79868, Ernst Taeuber, issued 1894

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[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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