Sodium Hydroxide → HCID 11770665, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of trifluoromethanesulfonic acid (15.3 mL, 173 mmol) at 0° C. was added N-(4-chlorobenzylidene)-2-phenylethanamine (3.38 g) and the reaction was heated to 120° C. and stirred 17 h under N2. The reaction was poured into ice water (100 mL) and basisified with 5N NaOH (45 mL). The aqueous layer was extracted with CH2Cl2 (3×100 mL). The combined organic layers were washed with saturated NaCl (100 mL), dried (MgSO4) and concentrated to give a yellow/brown oil. The residue was purified by ISCO (120 g SiO2, 0-50% EtOAc/hexane) to give 1-(4-chlorophenyl)-1,2,3,4-tetrahydroisoquinoline as a tan solid.

Provenance & Evidence