Methanol → HCID 66718521, compound

To a solution of 4-(4-methoxy-benzyl)-2-methyl-[1,4]oxazepane (1.66 g, 7.05 mmol) in 1,2-dichloroethane (12 ml) was added 1-chloroethyl chloroformate (2.52 g, 17.6 mmol) at room temperature. The mixture was refluxed for 5 hours and cooled to room temperature. After the addition of methanol (15 ml), the mixture was refluxed for 3 hours and concentrated in vacuo to afford the crude product. This crude product was partitioned between ether and 1N hydrochloric acid, and washed with ether. The water phase was basified with saturated aqueous sodium hydrogen carbonate. The product was extracted with dichloromethane. The organic layer was dried over sodium sulfate and the solvent was removed under reduced pressure carefully to avoid evaporating the product. To the resulting solution was added 4N hydrochloric acid in ethyl acetate. The solution was concentrated in vacuo to afford 2-methyl-[1,4]oxazepane hydrochloride as pale yellow oil (964 mg, 90%).

1. temperatureThe mixture was refluxed for 5 hours
2. temperaturethe mixture was refluxed for 3 hours
3. concentrationconcentrated in vacuo
4. customto afford the crude product
5. customThis crude product was partitioned between ether and 1N hydrochloric acid
6. washwashed with ether
7. extractionThe product was extracted with dichloromethane
8. dry with materialThe organic layer was dried over sodium sulfate
9. customthe solvent was removed under reduced pressure carefully
10. customto avoid evaporating the product
11. additionTo the resulting solution was added 4N hydrochloric acid in ethyl acetate
12. concentrationThe solution was concentrated in vacuo

ORD record

ord-5a88eed17aa6454c84ca2c19acb9cb3c

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108957B2