Dichloromethane → N-(2-cyclopentylethyl)-3-iodo-4-methylbenzamide

温度

0 °C

In a round-bottomed flask was charged 3-iodo-4-methylbenzoic acid (1.4 g, 5.4 mmol), dicloromethane (4 ml), and DMF (2 ml). This mixture was cooled to 0° C. and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.2 g, 6.3 mmol) was added. The reaction mixture was stirred for 10 min before 2-cyclopentylethanamine (0.47 g, 4.2 mmol) was introduced. The reaction mixture was stirred at 0° C. for 1 h, then at RT under N2 for 16 h. The reaction was partitioned between DCM (60 ml) and brine (50 mL). The aqueous layer was back exacted with DCM (4×20 mL) and the combined DCM layer was dried (Na2SO4) and concentrated. The crude product was dissolved in DCM and purified by chromatography through a Redi-sep pre-packed silica gel column (330 g), eluting with a gradient of 5% to 15% EtOAc in hexane, to provide N-(2-cyclopentylethyl)-3-iodo-4-methylbenzamide as a white solid. MS (ESI, pos. ion) m/z: 358.1 (M+1).

1. additionwas introduced
2. waitat RT under N2 for 16 h
3. customThe reaction was partitioned between DCM (60 ml) and brine (50 mL)
4. dry with materialthe combined DCM layer was dried (Na2SO4)
5. concentrationconcentrated
6. dissolutionThe crude product was dissolved in DCM
7. custompurified by chromatography through a Redi-sep pre-packed silica gel column (330 g)
8. washeluting with a gradient of 5% to 15% EtOAc in hexane

ORDレコード

ord-a03cb82b72a9475db1fd599e868448e7

出典データセット

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08492404B2