2-Chloro-N,N-dimethylethylamine → (S)-1-(3-((2-(Dimethylamino)ethoxy)methyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

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Reaction Conditions

Reaction Steps

To 2-chloro-N,N-dimethylethanamine (63 mg, 0.59 mmol) in DMF (1.0 mL) was added NaH (156 mg, 3.90 mmol, 60% suspension in mineral oil) at 0° C. After stirring for 20 min at 0° C., (S)-1-(3-(hydroxymethyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (40 mg, 0.20 mmol) was added, and the resulting suspension was stirred at room temperature for 10 min. TBAI (7 mg, 0.019 mmol) was then added, and the reaction mixture was heated at 70° C. for 1.5 h. The mixture was then poured into sat. aq. NH4Cl solution and EtOAc. The layers were separated, and the organic layer was washed with sat. aq. NH4Cl solution. The aqueous layer was extracted with EtOAc (3×), and the combined organics were washed with sat. aq. NaCl solution and dried over Na2SO4. Filtration and concentration in vacuo provided a crude oil which was triturated with hexanes (3×) to give the title compound (29 mg, 54%) as a pale yellow oil. MS(ESI+) m/z 206.1 (M+H)+.

Provenance & Evidence