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

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).

1. customfitted with a mechanical stirrer
2. temperaturereflux condenser and a dropping funnel at such a rate that the temperature
3. customdid not exceed 60° C
4. additionthe addition
5. waitwas continued for 1.5 hours
6. additionafter the addition
7. waitto stand overnight
8. extractionextracted with 3/×100 ml of ether
9. washThe pooled organic layer was washed with 2/×30 ml of brine
10. dry with materialdried over anhydrous MgSO4
11. filtrationThe solution was filtered
12. customthe ether removed under reduced pressure
13. custom50.4 g (69%) of 2-(N,N-dimethylaminomethyl)pyrrole was recovered

ORD record

ord-b4f7886b62744d889f1037c81f2d5387

Source dataset

uspto-grants-1988_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04746669