Isobucaine : Synthesis Wikipedia, the free encyclopedia

Isobucaine

Chemical compound

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

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.

Local anesthetics (primarily sodium channel blockers) (N01B)

Esters by acid

Aminobenzoic	Benzocaine Benzonatate Butacaine Butamben Chloroprocaine Dimethocaine Lucaine Meprylcaine Metabutethamine Metabutoxycaine Nitracaine Orthocaine Propoxycaine Procaine (Novocaine) Proxymetacaine Risocaine Tetracaine
Benzoic	Amylocaine Cocaine Cyclomethycaine α-Eucaine β-Eucaine Hexylcaine Isobucaine Piperocaine
ArCO2- (not para-amino or Ph)	Amoproxan (3,4,5-Trimethoxybenzoyl) 3-(p-Fluorobenzoyloxy)tropane