Chemistry:Isobucaine

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Short description: Chemical compound
Isobucaine
Isobucaine.svg
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC15H23NO2
Molar mass249.354 g·mol−1
3D model (JSmol)

Isobucaine is a local anesthetic.[1]

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

References

  1. Accepted Dental Remedies (26th ed.). Chicago: American Dental Association. 1961. p. 30. 
  2. "Esters of β-Alkylaminoethanols.". Journal of the American Chemical Society 67 (6): 933–939. June 1945. doi:10.1021/ja01222a017.