Diisopropylethylamine → 3-chloro-N-(3-dimethylamino-2,2-dimethyl-propyl)-4-nitro-benzamide

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Reaction Steps

3-chloro-4-nitro-benzoyl chloride (Intermediate 54; 2.2 g, 10.00 mmol) was dissolved in DCM (20 mL) and N,N-diisopropylethylamine (2.095 mL, 12.00 mmol) added. The mixture was cooled in an ice/water bath and N,N,2,2-tetramethyl-1,3-propanediamine (3.652 mL, 10.00 mmol) in DCM (10 mL) added dropwise. The mixture was allowed to warm to room temperature and stirred for 0.5 h. The mixture was washed with brine, 2N NaOH (aq.), dried (MgSO4) and concentrated. Column chromatography of the residue (2% MeOH/DCM) gave the title compound as a yellow oil 17171/2/1 (2.29 g, 77%).

Provenance & Evidence