Butacaine is a white crystalline ester used as a local anesthetic.[1] It was first marketed in the 1920s.[1]
Synthesis
The addition of metallic sodium to a mixture of allyl alcohol (1) and dibutylamine (2)[2] gives the conjugate addition product 3-dibutylamino-1-propanol (3). Reaction of this intermediate with p-nitrobenzoyl chloride (4) gives the ester 5. A Béchamp reduction of the nitro group completes the synthesis of butacaine (6).[3][4][5][6][7][8]
Synthesis of butacaine
See also
References
- 1 2 "Butacaine". Inxight Drugs. National Center for Advancing Translational Sciences.
- ↑ Kurihara, Tozaburo; Niwa, Hiroshi; Chiba, Katsuichi (1954). "Synthesis of γ-Alkylaminopropanols". Yakugaku Zasshi. 74 (7): 763–766. doi:10.1248/yakushi1947.74.7_763.
- ↑ Burnett, W. B.; Jenkins, R. L.; Peet, C. H.; Dreger, E. E.; Adams, Roger (1937). "Dialkylaminoalkanol Esters of p-Aminobenzoic Acid". Journal of the American Chemical Society. 59 (11): 2248–2252. doi:10.1021/ja01290a041.
- ↑ Kaye, Irving Allan; Roberts, I. Melville (1951). "Dialkylaminoalkyl Esters of 2-Amino-6-carboxybenzothiazole". Journal of the American Chemical Society. 73 (10): 4762–4764. doi:10.1021/ja01154a084.
- ↑ Oliver Kamm, Roger Adams, Volwiler Ernest H., U.S. patent 1,358,751 (1920 to Abbott Lab)
- ↑ Adams Roger, Ernest H Volwiler, U.S. patent 1,676,470 (1928 to Abbott Lab)
- ↑ Weston Arthur W, U.S. patent 2,437,984 (1948 to Abbott Lab)
- ↑ Anon., GB 191122 (1922-12-27 to Abbott Lab).