Benzaldehyde → HCID 3155259, compound

A mixture of 1-(3-aminopropyl)imidazole (Aldrich, 37.1 g, 297 mmol), benzaldehyde (30 g, 283 mmol), 3 Å molecular sieves (50 g), sodium acetate (24.1 g, 283 mmol) and anhydrous methanol (700 mL) are stirred at room temperature under N2 overnight. The mixture is cooled to 0° C. and sodium borohydride (10.9 g, 288 mmol) is added portionwise over 1 hour. The mixture is stirred at room temperature for 3 hours. The mixture is filtered through celite, washed with methanol, and concentrated in vacuo to give a residue which is diluted with dichloromethane and washed with 10% aqueous sodium hydroxide. The organic phases are washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the title compound as a pale yellow oil (56.3 g, MH+=216).

1. temperatureThe mixture is cooled to 0° C.
2. stirringThe mixture is stirred at room temperature for 3 hours
3. filtrationThe mixture is filtered through celite
4. washwashed with methanol
5. concentrationconcentrated in vacuo
6. customto give a residue which
7. washwashed with 10% aqueous sodium hydroxide
8. washThe organic phases are washed with brine
9. dry with materialdried over anhydrous magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-d4632895d9504fc19f7c36f088ab8cd7

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06432959B1