Water → HCID 14809088, compound

Temperature

70 °C

To a solution of 2′,6′-dihydroxy-acetophenone (500 mg, 3.28 mmol) in dimethylformamide (20 ml) were added potassium carbonate (680 mg, 4.93 mmol) and 1-bromo-3-chloropropane (0.34 ml, 3.45 mmol) and the mixture was stirred at 70° C. for 4 h. Water was added and the organics were extracted with ethylacetate, washed with brine, dried over sodium sulfate and concentrated to dryness. The residue was purified by flash chromatography over silica gel (gradient cyclohexane/ethyl acetate: 0-15%) to yield 6′-(3-chloropropoxy)-2′-hydroxy-acetophenone (348 mg, 46%) as a pale yellow solid. To a solution of 6′-(3-chloropropoxy)-2′-hydroxy-acetophenone (345 mg, 1.50 mmol) in acetonitrile (15 ml) was added potassium carbonate (416 mg, 3.0 mmol) and morpholine (0.396 ml, 4.52 mmol). The mixture was stirred for 18 hours at room temperature then 60° C. for 3 days. Water was added and the organics were extracted with ethylacetate, washed with brine, dried over sodium sulfate and concentrated to dryness. The residue was purified by flash chromatography over silica gel (gradient ethyl acetate/methanol: 0-10%) to yield 2′-hydroxy-6′-(3-morpholino-4-yl-propoxy)-acetophenone (171 mg, 40%) as an orange oil that solidified.

1. extractionthe organics were extracted with ethylacetate
2. washwashed with brine
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated to dryness
5. customThe residue was purified by flash chromatography over silica gel (gradient cyclohexane/ethyl acetate: 0-15%)

ORD record

ord-88e1829272474175b15c30f3136e1d70

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962627B2