N,N-Dimethylaniline → HCID 68519385, compound

Participants

Reaction Steps

89 mg of 3-benzyl-1,2,3,4-tetrahydroisoquinoline obtained in Example 1-d) was dissolved in 2 mL of methylene chloride, and 53 mg of N,N-dimethylaniline, 73 mg of bromoacetylbromide were added thereto, followed by stirring under ice-cooling for 30 minutes. After completion of the reaction, water was added thereto, followed by extraction with chloroform. The chloroform layer was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was removed by evaporation, followed by purification using PLC (hexane:ethyl acetate=1:1) to obtain 120 mg (yield 88%) of 2-(2-bromoacetyl)-3-benzyl-1,2,3,4-tetrahydroisoquinoline as a yellow oily substance. 34 mg of this product was dissolved in 10 mg of aniline, 15 mg of potassium carbonate, and 1 mL of acetonitrile, followed by stirring at 60° C. for 4 hours. After completion of the reaction, the reaction liquid was filtered with ethyl acetate, concentrated under reduced pressure, and purified using PTLC (chloroform:methanol=10:1) to obtain 28 mg (yield 72%) of a title compound as a yellow oily substance.

Provenance & Evidence