Sodium Hydroxide → HCID 9951860, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 6,7-methylenedioxy-4-(3,4-ethylenedioxyphenyl)-quinazolin-2-one (400 mg, 1.29 mmol) in DMF (15 mL) was added KOtBu (95%, 232 mg, 2.06 mmol) at room temp. and stirred for 45 minutes. Separately, a solution of 2-dimethylaminoethyl chloride hydrochloride (371 mg, 2.58 mmol) in benzene (12 mL) was treated with a solution of 2 N NaOH (10 mL). The benzene layer, which contained the free base, was dried over anhydrous MgSO4, and added to the above reaction mixture at room temp. The resulting mixture was then heated at 110° C. under argon gas for 15 h. The reaction mixture was then poured into ice-water (50 mL). It was stirred for 30 minutes. The resulting precipitate was collected by filtration. It was dissolved in ethyl acetate. The organic layer was washed with water and brine. After being dried over anhydrous MgSO4 the solvent was removed in vacuo. This crude product was then dissolved in a small amount of CHCl3 and poured on a column of silica gel. Elution with acetone:CH2Cl2:MeOH (90:5:5) gave 6,7-methylenedioxy-4-(3,4-methylenedioxyphenyl)-2-(2-(dimethylamino) ethoxy)-quinazoline as a first fraction as yellow solid (110 mg); C21H21N3O5; mp120-123° C. 1H NMR (CDCl3) δ 7.33 (s, 1H), 7.20-7.27 (m, 2H), 7.14 (s, 1H), 6.95 (d, J=7.80 Hz, 1H), 6.08 (s, 2H), 4.59 (m, 2H), 4.32 (s, 4H), 2.83 (m, 2H), 2.38 (s, 6H). Further elution with the same solvent mixture gave 1-(2-(dimethylamino)ethyl)-6,7-methylenedioxy-4-(3,4-ethylenedioxyphenyl)-quinazolin-2(1H)-one as pale yellow solid (90 mg); C21H21N3O5; mp 220-225° C. 1H NMR (CDCl3) δ 7.24 (s, 1H), 7.23 (s, 1H), 7.16-7.19 (m, 2H), 6.95 (d, J=8.4 Hz, 1H), 6.09 (s, 2H), 4.40 (m, 2H), 4.31 (s, 4H), 2.76 (m, 2H), 2.43 (s, 6H).

Provenance & Evidence