Carbon Dioxide → N-(2-Aminoethyl)-N-(4-chlorophenyl)amine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

The hydrochloride salt of 4-chloroaniline (6.2 g, 38 mmol) and 2-oxazolidone (3.29 g, 38 mmol) was suspended in a minimal amount of di(ethyleneglycol)methyl ether and the resulting suspension heated at 160° C. After 4 h CO2 evolution ceased and the reaction mixture was cooled to ambient temperature. The resulting solid was crystallized from EtOH/ether to yield 4.6 g (58%) of 4-chloroanilinoethylamine as its HCl salt. MS (CI) (M+H)+ at m/z 171. The free amine was prepared by partitioning the HCl salt between CH2Cl2 and NaHCO3 (sat.), drying the organic layer (Na2SO4), filtering and concentrating.

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