Isobucaine

Isobucaine
Identifiers
	IUPAC name [2-methyl-2-(2-methylpropylamino)propyl] benzoate;
CAS Number	14055-89-1 ;
PubChem CID	26427;
ChemSpider	24619 ;
UNII	2XV8GIV746;
CompTox Dashboard (EPA)	DTXSID20161440 ;
Chemical and physical data
Formula	C15H23NO2
Molar mass	249.354 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)CNC(C)(C)COC(=O)c1ccccc1;
	InChI InChI=1S/C15H23NO2/c1-12(2)10-16-15(3,4)11-18-14(17)13-8-6-5-7-9-13/h5-9,12,16H,10-11H2,1-4H3 ; Key:YGSFZBYOMFZJPV-UHFFFAOYSA-N ;

Isobucaine is a local anesthetic.^[1]

Synthesis

The reductive amination between aminomethyl propanol (1) and isobutanal [78-84-2] (2) afforded N-Isobutyl-1,1-dimethyl-2-hydroxyethanamine, CID:18315986 (3). Acylation of the amine with benzoyl chloride [98-88-4] hypothetically goes initially to the amide (4'). The acid catalysis used in the reaction leads to an N to O acyl migration to afford isobucaine (5).

References

^ Thoma KH (1961). Accepted Dental Remedies (26th ed.). Chicago: American Dental Association. p. 30.
^ Reasenberg JR, Goldberg SD (June 1945). "Esters of β-Alkylaminoethanols". Journal of the American Chemical Society. 67 (6): 933–939. doi:10.1021/ja01222a017.

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[1] Thoma KH (1961). Accepted Dental Remedies (26th ed.). Chicago: American Dental Association. p. 30.

[2] Reasenberg JR, Goldberg SD (June 1945). "Esters of β-Alkylaminoethanols". Journal of the American Chemical Society. 67 (6): 933–939. doi:10.1021/ja01222a017.

[1]

[2]

Synthesis

See also

References