Benzaldehyde → 1-Benzylpiperidine-3-carboxylic acid

Nipecotic acid (1.31 g, 10.2 mmol), benzaldehyde (1.12 g, 10.6 mmol) and 5% palladium-carbon (0.18 g) in methanol (10 mL) was stirred at room temperature for one day under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in methanol (50 mL) was stirred with benzaldehyde (4.40 g, 41.5 mmol) and 5% palladium-carbon (0.118 g) at room temperature for one day. The reaction mixture was filtered, and the filtrated was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform/methanol=10/1→5/1 (v/v)) to give the title compound as a colorless oil (1.41 g, yield 63%).

1. filtrationThe reaction mixture was filtered
2. concentrationthe filtrate was concentrated under reduced pressure
3. dissolutionThe resulting residue was dissolved in methanol (50 mL)
4. filtrationThe reaction mixture was filtered
5. concentrationthe filtrated was concentrated under reduced pressure
6. customThe resulting residue was purified by silica gel column chromatography (chloroform/methanol=10/1→5/1 (v/v))

ORD record

ord-7c5832dee0184dcb842589dda9326d3f

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216999B2