Butacaine Explained

Butacaine is a white crystalline ester used as a local anesthetic.^[1] It was first marketed in 1920.^[1]

Synthesis

The addition of metallic sodium is added to a mixture of allyl alcohol (1) and dibutylamine (2)^[2] gives the conjugate addition product 3-dibutylamino-1-propanol (3). Esterification of this intermediate with para-nitrobenzoyl chloride (4) gives the ester 5. The reduction of the nitro group completes the synthesis of butacaine (6).^{[3] [4] [5] [6] [7] [8]}

See also

• Isobucaine

Notes and References

1. Web site: Butacaine . Inxight Drugs . National Center for Advancing Translational Sciences .
2. 10.1248/yakushi1947.74.7_763 . Synthesis of γ-Alkylaminopropanols . 1954 . Kurihara . Tozaburo . Niwa . Hiroshi . Chiba . Katsuichi . Yakugaku Zasshi . 74 . 7 . 763–766 .
3. 10.1021/ja01290a041 . Dialkylaminoalkanol Esters of p-Aminobenzoic Acid . 1937 . Burnett . W. B. . Jenkins . R. L. . Peet . C. H. . Dreger . E. E. . Adams . Roger . Journal of the American Chemical Society . 59 . 11 . 2248–2252 .
4. 10.1021/ja01154a084 . Dialkylaminoalkyl Esters of 2-Amino-6-carboxybenzothiazole . 1951 . Kaye . Irving Allan . Roberts . I. Melville . Journal of the American Chemical Society . 73 . 10 . 4762–4764 .
5. Oliver Kamm, Roger Adams, Volwiler Ernest H., (1920 to Abbott Lab)
6. Adams Roger, Ernest H Volwiler, (1928 to Abbott Lab)
7. Weston Arthur W, (1948 to Abbott Lab)
8. Anon., (1922-12-27 to Abbott Lab).