Diisopropylamine → 10-Oxo-10,11-dihydro-dibenzo[b,f]azepine-5-carboxylic acid methyl ester

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Reaction Conditions

Reaction Steps

Diisopropylamine (11.66 g, 0.115 mol, 1.2 eq.) is dissolved in THF (150 mL) and the solution is cooled down to −10° C. A solution of n-Butyllithium in hexane (72 mL of a 1.6 M solution, 1.2 eq.) is added slowly in order to keep the temperature below 0° C. (40 min). A solution of (2-dimethylcarbamoyl-phenyl)-o-tolyl-carbamic acid methyl ester (30.2 g, 0.096 mol, 1 eq.) in THF (80 mL) is added in 45 min. to the obtained solution. The reaction mixture is stirred for 1 hour at −5° C. before quenching by addition of water (30 mL). The mixture is concentrated in vacuum and water (220 mL) and ethylacetate (220 mL) are added to the oily residue. The phases are stirred rapidly before letting them separate. The organic phase is washed with aqueous sulfuric acid (300 mL of 1-M solution) and twice with water (300 mL). The organic phase is evaporated to dryness and delivers 23.0 g (89.5% yield) of the title compound as an orange oil that solidifies on standing.

Provenance & Evidence