Morpholine → 4-(4-Bromobenzoyl)morpholine

1-Hydroxybenzotriazole (2.02 g, 14.9 mmol) and 2.86 g (14.9 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added to a solution of 2.0 g (9.95 mmol) of 4-bromobenzoic acid in N,N-dimethylformamide (15 ml), and the mixture was stirred at room temperature for 10 min. Thereafter, 1.3 ml (14.9 mmol) of morpholine was added thereto, and the mixture was stirred at room temperature for 18 hr. The reaction was stopped by adding a saturated aqueous sodium hydrogencarbonate solution, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with water and saturated brine in that order, was dried over anhydrous sodium sulfate, and was then filtered. The filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2) to give 2.66 g (yield 99%) of the title compound.

1. stirringthe mixture was stirred at room temperature for 18 hr
2. extractionthe reaction solution was extracted with ethyl acetate
3. washThe organic layer was washed with water and saturated brine in that order
4. dry with materialwas dried over anhydrous sodium sulfate
5. filtrationwas then filtered
6. concentrationThe filtrate was concentrated under the reduced pressure
7. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2)

ORD record

ord-8dd5848e414b4f0e8b798d36a03f0e81

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07871982B2