Dimethylamine → HCID 67505515, compound

To a solution of N-[4-chloro-2-(2-methyl-benzoyl)-phenyl]-benzamide (5.1 g, 14.6 mmol) and N-bromosuccinimide (2.85 g, 16 mmol) in CCl4 (150 mL) was added 2,2′-azobisisobutrylnitrile (0.2 g, 1.5 mmol). The solution was refluxed for 4 h. The solution was then cooled to room temperature, diluted with CH2Cl2 (150 mL) and washed with H2O (3×50 mL). The organic portion was dried over Na2SO4 and evaporated to dryness in vacuo to provide N-[2-(2-bromomethyl-benzoyl)-4-chloro-phenyl]-benzamide (4.6 g, 74%). A solution of the benzamide (2.3 g, 5.4 mmol) in CH2Cl2 (50 mL) was saturated with dimethylamine, stirred for 16 h and evaporated to dryness in vacuo. The resulting residue was dissolved in MeOH (50 mL) and KOH (0.9 g, 16 mmol) in H2O (5 mL) was added. The solution was refluxed for 24 h. The solution was concentrated in vacuo and then diluted with EtOAc (150 mL) and H2O (50 mL). The organic portion was washed with H2O (3×50 mL), dried over Na2SO4 and purified by column chromatography (silica gel, 18:80.2 MeOH:CH2Cl2:NHOH) to provide lq (0.9 g, 53% yield) MS m/z=289 (M+H).

1. customevaporated to dryness in vacuo
2. dissolutionThe resulting residue was dissolved in MeOH (50 mL)
3. temperatureThe solution was refluxed for 24 h
4. concentrationThe solution was concentrated in vacuo
5. additiondiluted with EtOAc (150 mL) and H2O (50 mL)
6. washThe organic portion was washed with H2O (3×50 mL)
7. dry with materialdried over Na2SO4
8. custompurified by column chromatography (silica gel, 18:80.2 MeOH:CH2Cl2:NHOH)
9. customto provide lq (0.9 g, 53% yield)

ORD record

ord-c043f194bdcf491984aeb9b40442497e

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399659B2