Triethylamine → HCID 66718654, compound

Temperature

0 °C

To a solution of 3-(4-methoxy-benzylamino)-propan-1-ol (2.00 g, 10.2 mmol) in dichloromethane (30 ml) was added triethylamine (1.09 g, 10.8 mmol) and 2-chloropropionyl chloride (1.37 g, 10.8 mmol) at 0° C. The mixture was stirred at 0° C. for one hour and partitioned between 0.5N hydrochloric acid and dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was dissolved into 2-propanol (50 ml) and potassium hydroxide (1.15 g, 20.5 mmol) was added at 0° C. The resulting mixture was stirred at 0° C. for 4 hours and partitioned between saturated ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=3/1) to afford 4-(4-methoxybenzyl)-2-methyl-[1,4]oxazepan-3-one as colorless oil (2.00 g, 78%).

1. custompartitioned between 0.5N hydrochloric acid and dichloromethane
2. washThe organic layer was washed with brine
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated in vacuo
5. additionwas added at 0° C
6. stirringThe resulting mixture was stirred at 0° C. for 4 hours
7. custompartitioned between saturated ammonium chloride solution and ethyl acetate
8. washThe organic layer was washed with brine
9. dry with materialdried over sodium sulfate
10. concentrationconcentrated in vacuo
11. customThe residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=3/1)

ORD record

ord-32035f3e702c4cb79fb967634ef75f59

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108957B2