Benzocaine → 4-(1-Cyano-cyclohexylamino)benzoic acid ethyl ester

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Reaction Steps

2 g (12.1 mmol, 1 eq.) of ethyl 4-aminobenzoate (Starting material 1) are added to a solution of 1.25 g (12.1 mmol, 1 eq.) of cyclohexanone (Starting material 2) in 20 ml of acetic acid at 0° C. The solution is stirred for 15 minutes, and 1.6 ml (12 mmol, 1 eq.) of trimethylsilyl cyanide are added. The reaction medium is stirred for 5 hours at room temperature. It is then poured gently into ice-cold ammonium hydroxide solution and extracted with ethyl acetate. The organic phases are combined and washed with water. They are dried over sodium sulfate. The residue is precipitated from dichloromethane and heptane. The product 4-(1-cyano-cyclohexylamino)benzoic acid ethyl ester is obtained in the form of a white solid.

Provenance & Evidence