[CH2:1]=O.Cl.[CH3:4][NH:5][CH3:6].[CH2:7]([N:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1)[CH3:8].[OH-].[Na+]>CCOCC>[CH3:4][N:5]([CH2:1][C:10]1[N:9]([CH2:7][CH3:8])[CH:13]=[CH:12][CH:11]=1)[CH3:6]
A mixture of a 35% aqueous formaldehyde solution (9.0 mL, 105 mmol) and dimethylamine hydrochloride (9.0 g, 110 mmol) was added to 1-ethylpyrrol (10.0 g, 105 mmol) under ice-cooling with stirring over 1 hour and 30 minutes and the mixture was stirred at room temperature for 6 hours. A 10% aqueous sodium hydroxide solution (150 mL) and ether were added to the reaction mixture to separate it. The thus obtained organic phase was separated, washed with a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (methylene chloride:methanol, 9:1) to obtain 2-(N,N-dimethylaminomethyl)-1-ethylpyrrol (15.6 9, yield: 97%).
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