Sodium hydride → 1-(5-bromo-1,3-benzodioxol-4-yl)-N-[2-(pyrrolidin-1-yl)ethoxy]methanimine

To a stirred solution of 5-bromo-1,3-benzodioxole-4-carbaldehyde oxime (0.244 g, 1 mmol) in dry DMF (15 ml), 1-(2-chloroethyl)pyrrolidine hydrochloride (0.207 g, 1.22 mmol) and NaH (0.138 g, 3.45 mmol, 60% dispersion in oil) were added. The reaction mixture was stirred at ambient temperature for 5 minutes and then heated at 80° C. overnight. Then the reaction mixture was cooled to ambient temperature and quenched with methanol (4 ml). After evaporation of the solvent in vacuo, water (25 ml) was added to the residue, and the mixture was extracted with dichloromethane (2×25 ml). The combined organic phases were dried over anhydrous MgSO4. The solvent was evaporated in vacuo, and the residue was purified by column chromatography with a mixture of chloroform:ethyl acetate (10:1) as the eluent. After the isolation of the unreacted starting material, the eluent was changed to ethyl acetate:isopropanol:cc. NH3 (9:1:0.5). The crude product was digerated with water.

1. temperatureheated at 80° C. overnight
2. temperatureThen the reaction mixture was cooled to ambient temperature
3. customquenched with methanol (4 ml)
4. customAfter evaporation of the solvent in vacuo, water (25 ml)
5. additionwas added to the residue
6. extractionthe mixture was extracted with dichloromethane (2×25 ml)
7. dry with materialThe combined organic phases were dried over anhydrous MgSO4
8. customThe solvent was evaporated in vacuo
9. customthe residue was purified by column chromatography with a mixture of chloroform:ethyl acetate (10:1) as the eluent

ORDレコード

ord-29311f4607b74a5cb83278a9ef8b51d8

出典データセット

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08536210B2