4-Methylmorpholine → Methyl 3-(dimethylcarbamoyl)benzoate

To a methylene chloride (20 ml) solution of monomethyl isophthalate (317 mg, 1.76 mmol) were added dimethylamine hydrochloride (172 mg, 2.11 mmol), 1-hydroxybenzotriazole (287 mg, 1.76 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (404 mg, 2.11 mmol) and N-methylmorpholine (0.23 ml, 2.11 mmol) and the resulting mixture was stirred at room temperature for 21 hours. The reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue. The resulting mixture was washed successively with 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate, and brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column and the fraction obtained from the methanol:methylene chloride (=1:50) eluate was concentrated under reduced pressure, whereby the title compound (290 mg, 80%) was obtained as a colorless oil.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionEthyl acetate was added to the residue
3. washThe resulting mixture was washed successively with 1N hydrochloric acid
4. dry with materiala saturated aqueous solution of sodium bicarbonate, and brine, and dried over anhydrous sodium sulfate
5. filtrationAfter filtration
6. concentrationthe filtrate was concentrated under reduced pressure
7. customthe fraction obtained from the methanol
8. concentrationmethylene chloride (=1:50) eluate was concentrated under reduced pressure, whereby the title compound (290 mg, 80%)
9. customwas obtained as a colorless oil

ORD record

ord-6cce3094c4d84e379834210cd13fa452

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07399775B2