Isobucaine
Identifiers
  • [2-methyl-2-(2-methylpropylamino)propyl] benzoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H23NO2
Molar mass249.354 g·mol−1
3D model (JSmol)
  • CC(C)CNC(C)(C)COC(=O)c1ccccc1
  • 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 checkY
  • Key:YGSFZBYOMFZJPV-UHFFFAOYSA-N checkY

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

References

  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.
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