Sodium hydride → HCID 53409892, compound

tert-Butyl 4-hydroxypiperidine-1-carboxylate (1.0 g) was mixed with DMF (15 ml), and sodium hydride (55% suspended in oil) (300 mg) was added thereto, followed by stirring at room temperature for 10 minutes. To the reaction mixture was added 1-bromo-3-methoxypropane (1.0 g), followed by stirring at room temperature overnight. Water was added to the reaction mixture, and the reaction mixture was concentrated under reduced pressure. EtOAc and water were added to the obtained residue, and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc). The purified product thus obtained was mixed with EtOH (10 ml), and a 4M hydrogen chloride/dioxane (10 ml) was added thereto, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure to obtain 4-(3-methoxypropoxy)piperidine hydrochloride (302 mg).

1. additionwas added
2. stirringby stirring at room temperature overnight
3. concentrationthe reaction mixture was concentrated under reduced pressure
4. additionEtOAc and water were added to the obtained residue
5. dry with materialthe organic layer was dried over Na2SO4
6. concentrationconcentrated under reduced pressure
7. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)
8. customThe purified product thus obtained
9. stirringby stirring at room temperature overnight
10. concentrationThe reaction mixture was concentrated under reduced pressure

ORD record

ord-5b25fcd55e854e7ea359293cffa52803

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09051283B2