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

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). the resulting mixture was stirred at room temperature for 2 hours After stirring the reaction mixture was extracted with dichloromethane The extract was washed with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate After filtration the solvent was removed in vacuo the residue was purified by chromatography on a silica gel column

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). the resulting mixture was stirred at room temperature for 2 hours After stirring the reaction mixture was extracted with dichloromethane The extract was washed with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate After filtration the solvent was removed in vacuo the residue was purified by chromatography on a silica gel column

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). the resulting mixture was stirred at room temperature for 2 hours After stirring the reaction mixture was extracted with dichloromethane The extract was washed with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate After filtration the solvent was removed in vacuo the residue was purified by chromatography on a silica gel column

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-(dimethylaminomethyl)pyrrole (24.8 g) and imidazole (13.6 g) in xylene (120 ml) are heated under reflux for 3 hours. The solution was cooled and the solid was filtered off and crystallised from ether to give 2-(imidazol-1-ylmethyl) pyrrole (15.3 g), m.p. 89°-90°, raised to 91°-92° on further crystallisation from water. under reflux for 3 hours The solution was cooled the solid was filtered off crystallised from ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-(dimethylaminomethyl)pyrrole (24.8 g) and imidazole (13.6 g) in xylene (120 ml) are heated under reflux for 3 hours. The solution was cooled and the solid was filtered off and crystallised from ether to give 2-(imidazol-1-ylmethyl) pyrrole (15.3 g), m.p. 89°-90°, raised to 91°-92° on further crystallisation from water. under reflux for 3 hours The solution was cooled the solid was filtered off crystallised from ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). the resulting mixture was stirred at room temperature for 2 hours After stirring the reaction mixture was extracted with dichloromethane The extract was washed with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate After filtration the solvent was removed in vacuo the residue was purified by chromatography on a silica gel column

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). the resulting mixture was stirred at room temperature for 2 hours After stirring the reaction mixture was extracted with dichloromethane The extract was washed with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate After filtration the solvent was removed in vacuo the residue was purified by chromatography on a silica gel column

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cold solution of 67 g (0.47 mole) of methyliodide in 150 ml of anhydrous ether was added slowly a dry ether solution of 50 gm of 2-(N,N-dimethylaminomethyl)pyrrole (0.37 mole). A white solid begain to precipitate out of solution. The mixture was heated to 30° for 1.5 hours, filtered and washed with 2/×30 ml of ether to obtain 59 gm of 2-pyrryl)methyltrimethylammonium iodide which was used in the next step without further purification. A white solid begain to precipitate out of solution The mixture was heated to 30° for 1.5 hours filtered washed with 2/×30 ml of ether to obtain 59 gm of 2-pyrryl)methyltrimethylammonium iodide which was used in the next step without further purification

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 42.5 g (0.52 mole) of dimethylamine hydrochloride in 41 g of 38% formaldehyde (0.525 mole) was added slowly to 36.5 g (0.50 mole) of pyrrole in a 3-neck round-bottomed flask, fitted with a mechanical stirrer, reflux condenser and a dropping funnel at such a rate that the temperature did not exceed 60° C. About 30 to 60 minutes was needed to complete the addition. Stirring was continued for 1.5 hours after the addition was completed. The mixture was allowed to stand overnight. Then it was poured into 100 ml of 25% sodium hydroxide and extracted with 3/×100 ml of ether. The pooled organic layer was washed with 2/×30 ml of brine and dried over anhydrous MgSO4. The solution was filtered and the ether removed under reduced pressure. 50.4 g (69%) of 2-(N,N-dimethylaminomethyl)pyrrole was recovered, (b.p. 88°-100° C. at 19 mm Hg). fitted with a mechanical stirrer reflux condenser and a dropping funnel at such a rate that the temperature did not exceed 60° C the addition was continued for 1.5 hours after the addition to stand overnight extracted with 3/×100 ml of ether The pooled organic layer was washed with 2/×30 ml of brine dried over anhydrous MgSO4 The solution was filtered the ether removed under reduced pressure 50.4 g (69%) of 2-(N,N-dimethylaminomethyl)pyrrole was recovered

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). the resulting mixture was stirred at room temperature for 2 hours After stirring the reaction mixture was extracted with dichloromethane The extract was washed with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate After filtration the solvent was removed in vacuo the residue was purified by chromatography on a silica gel column

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). the resulting mixture was stirred at room temperature for 2 hours After stirring the reaction mixture was extracted with dichloromethane The extract was washed with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate After filtration the solvent was removed in vacuo the residue was purified by chromatography on a silica gel column

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-(dimethylaminomethyl)pyrrole (24.8 g) and imidazole (13.6 g) in xylene (120 ml) are heated under reflux for 3 hours. The solution was cooled and the solid was filtered off and crystallised from ether to give 2-(imidazol-1-ylmethyl) pyrrole (15.3 g), m.p. 89°-90°, raised to 91°-92° on further crystallisation from water. under reflux for 3 hours The solution was cooled the solid was filtered off crystallised from ether