Borane → HCID 28657291, compound

To a solution of 4-methoxy-N-(3-piperidin-1-ylpropyl)benzamide (1.9 g, 6.9 mmol) in THF (15 mL) was added borane*THF (1M in THF, 10 mL, 10 mmol) and the reaction mixture heated at reflux temperature for 18 h. The solution was cooled to room temperature and quenched with 4N HCl/dioxane (2 mL). The product mixture was washed with diethyl ether (2×50 mL) and basified with 40% (w/w) KOH (aq.). The aqueous layer was extracted with dichloromethane (3×50 mL) and the organic phase dried (Na2SO4) and concentrated in vacuo. The resultant oil was purified by chromatography on silica gel with methanol:dichloromethane (1:9, v/v) as eluent to afford N-(4-methoxybenzyl)-3-piperidin-1-ylpropan-1-amine (INTERMEDIATE IX.1) (400 mg, 1.5 mmol, 22%).

1. temperaturethe reaction mixture heated
2. temperatureat reflux temperature for 18 h
3. customquenched with 4N HCl/dioxane (2 mL)
4. washThe product mixture was washed with diethyl ether (2×50 mL)
5. extractionThe aqueous layer was extracted with dichloromethane (3×50 mL)
6. dry with materialthe organic phase dried (Na2SO4)
7. concentrationconcentrated in vacuo
8. customThe resultant oil was purified by chromatography on silica gel with methanol:dichloromethane (1:9, v/v) as eluent

ORD record

ord-89f3402f6aa4469c95a61f14124f35c6

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07807686B2