Formaldehyde → 6-Methoxy-1,2,3,4-tetrahydroisoquinoline

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Reaction Steps

To the solution of 3-methoxylphenethylamine (15.1 g, 0.1 mol) in formic acid (100 ml) at rt is added paraformaldehyde (3.0 g, 0.1 mol, 1.0 eq.). The resulting mixture is stirred at 40˜50° C. for 24 hr. After the reaction is completed, the formic acid is evaporated and the residue is diluted with water (200 ml), basified with sodium hydroxide solution (10.0N, 10.5 ml) to pH=10, and extracted with EtOAc. The combined organic layers are washed with water and brine and dried over sodium sulfate, and the solvent is removed under reduced pressure to give the title compound. MS (+VE) m/z 164.1 (M++1).

Provenance & Evidence