Hydrochloric Acid → 2-Methyl-1-phenylpropan-1-amine

Participants

Reaction Conditions

Reaction Steps

To 2-methoxy-N-(2-methyl-1-phenylpropyl)aniline (1.36 g, 5.34 mmol, 1.00 equiv) in 2:1 v/v MeCN/H2O (76 mL) was added AgNO3 (0.271 g, 1.60 mmol, 0.300 equiv) and the reaction mixture was heated to 60° C. Ammonium persulfate (8.58 g, 37.6 mmol, 7.04 equiv) was added in three portions over 15 min and the reaction mixture was heated at 60° C. for 1 h. An aqueous solution of HCl (10 mL, 2 N in H2O) was added. The reaction mixture was filtered through a celite pad, eluting with H2O. The aqueous layer was washed with Et2O (3×30 mL) and the combined organic layers were washed with HCl (2×30 mL, 0.5 N in H2O). The combined aqueous layers were basified with 2.5 M NaOH and the aqueous layer was extracted with Et2O (4×20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by Kugelrohr distillation (50 mTorr, 60° C.) to give 2-methyl-1-phenylpropan-1-amine as a colorless oil (0.257 g, 32% yield).

Provenance & Evidence