Hydrochloric Acid → 1-(4-(Morpholinomethyl)phenyl)ethanone

温度

0 °C

To a stirred suspension of 4-(morpholinomethyl)benzonitrile (preparation 5) (1.00 g, 5 mmol) in toluene (19 ml), 3M methyl magnesium bromide in ethyl ether (5 ml, 15 mmol) was added at room temperature under argon. The resulting suspension was refluxed for 4 h, allowed to reach room temperature and then cooled down to 0° C., acidified with 10% HCl and then heated to reflux for 1 h. The two phases were separated and the aqueous phase rinsed with ethyl acetate, then brought to pH 10 with NH4OH and extracted with DCM. The phases were separated and the organic phase was dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography using an 80 g silica gel cartridge and eluting with DCM (Solvent A) and MeOH (Solvent B) and the following gradient: 1 min hold 100% A followed by a 12 min ramp to 2.5% B and then 5 min hold at 2.5% B. The desired fractions were concentrated to dryness under vacuum to obtain the desired compound as a white solid (0.79 g, 3.6 mmol, Yield: 70%).

1. additionwas added at room temperature under argon
2. temperatureThe resulting suspension was refluxed for 4 h
3. customto reach room temperature
4. temperatureheated
5. temperatureto reflux for 1 h
6. customThe two phases were separated
7. washthe aqueous phase rinsed with ethyl acetate
8. extractionextracted with DCM
9. customThe phases were separated
10. dry with materialthe organic phase was dried over MgSO4
11. concentrationconcentrated under reduced pressure
12. customThe crude product was purified by flash column chromatography
13. washeluting with DCM (Solvent A) and MeOH (Solvent B)
14. custom1 min
15. custom5 min
16. concentrationThe desired fractions were concentrated to dryness under vacuum

ORDレコード

ord-33fdcec570074b98b29ff094d2e5dd89

出典データセット

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09115088B2