Formaldehyde → N,N-dimethyl-1-(1H-pyrrol-2-yl)methanamine

A mixture of 35% aqueous formaldehyde solution (3.2 ml, 40.7 mmol) and dimethylamine hydrochloride (3.44 g, 42.4 mmol) was added to pyrrole (2.72 g, 40.47 mmol) at room temperature with stirring over a 20-minute interval, and the resulting mixture was stirred at room temperature for 2 hours. After stirring, 10% aqueous sodium hydroxide solution (18 ml) was added to the reaction mixture, and the reaction mixture was extracted with dichloromethane. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of dichloromethane and methanol (10:1) as the eluent to afford 2-(N,N-dimethylaminomethyl)pyrrole (4.55 g, quantitative yield).

1. stirringthe resulting mixture was stirred at room temperature for 2 hours
2. stirringAfter stirring
3. extractionthe reaction mixture was extracted with dichloromethane
4. washThe extract was washed with saturated aqueous sodium chloride solution
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationAfter filtration
7. customthe solvent was removed in vacuo
8. customthe residue was purified by chromatography on a silica gel column

ORD record

ord-c9c061f5073f415aab32425d07acee14

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08101650B2