Butacaine

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

Synthesis
The addition of metallic sodium is added to a mixture of allyl alcohol (1) and dibutylamine (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).


 * Butacaine synthesis.svg