Sodium Hydroxide → N-[4-Chloro-3-(2-dimethylaminoethoxy)phenyl]aminoacetaldehyde dimethyl acetal

Participants

Reaction Steps

To a suspension of 4-chloro-3-(2-dimethylaminoethoxy)aniline (D6, 1.22 g, 0.006 mol) in McOH (30 ml) containing dimethoxyethanal in MTBE (1.76 g, 0.17 mol) and glacial acetic acid (1.71 g) was added sodium cyanoborohydride (1.78 g, 0.03 mol) portionwise at 0 C. After addition, the reaction was left to stir at room temperature for 1 hour, and then 10% aqueous NaOH was added and the mixture was extraced with CH2Cl2 and the combined organic layers were dried (Na2SO4), and concentrated in vacuo to give a brown oil. Purification by FCC, eluting with CH2Cl2 gave the title compound (1.49 mg, 87% )

Provenance & Evidence