Aluminium lithium hydride → 4-[N-(7-Hydroxy-3-oxahept-1-yl)-N-(isopropyl)amino]-1-benzylpiperidine

To a solution of N-(1-benzylpiperidin-4-yl)-N-isopropyl 2-(4-hydroxybut-1-oxy)acetamide (4.7 g, 13 mmol) in THF (30 mL) was slowly added 1 M lithium aluminum hydride in THF (20 mL, 19.5 mmol) at 0° C. The reaction mixture was stirred at room temperature overnight and then quenched by slow addition of 15% aqueous sodium hydroxide at 0° C. until no gas formation was observed. After stirring for 10 minutes at room temperature, a solid formed and the reaction mixture was filtered and the precipitate washed with THF three times. The filtrate was then concentrated and the residue was dissolved in dichloromethane and this solution was washed with brine, dried over magnesium sulfate and concentrated in vacuo to give 3.71 g of the title intermediate (82% yield).

1. customat 0° C
2. customquenched by slow addition of 15% aqueous sodium hydroxide at 0° C. until no gas formation
3. stirringAfter stirring for 10 minutes at room temperature
4. customa solid formed
5. filtrationthe reaction mixture was filtered
6. washthe precipitate washed with THF three times
7. concentrationThe filtrate was then concentrated
8. dissolutionthe residue was dissolved in dichloromethane
9. washthis solution was washed with brine
10. dry with materialdried over magnesium sulfate
11. concentrationconcentrated in vacuo

ORD record

ord-e68ecf56542742c7862dea3537b0480c

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080565B2