Isobucaine

Isobucaine is a local anesthetic.^[1]

Isobucaine

Identifiers
IUPAC name [2-methyl-2-(2-methylpropylamino)propyl] benzoate
CAS Number	14055-89-1 Y
PubChem CID	26427
ChemSpider	24619 Y
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 Y Key:YGSFZBYOMFZJPV-UHFFFAOYSA-N Y

Synthesis

Synthesis:^[2]

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).

See also

• List of local anesthetics