Benzyl Bromide → HCID 15136430, compound

Temperature

0 °C

To a mixture of 1H-pyrrol-1-amine (9.2 g, 0.112 mole) and NaHCO3 (15 g, 0.19 mole) in 50 ml dichloromethane (DCM) at 0° C., was added ethyl chloroformate (11.4 ml, 0.12 mole) in fifteen minutes. After stirring at 0° C. for one hour, then at ambient temperature for four hours, the mixture was filtered and the filtrate was washed with water, then dried (saturated NaCl solution, anhydrous MgSO4). After filtering, the solvent was evaporated to give a solid, 17 g (95%), m.p. 60°-61° C., of N-(1H-pyrrol-1-yl) carbamic acid ethyl ester. To a solution of N-(1H-pyrrol-1-yl) carbamic acid ethyl ester (9.0 g, 0.058 mole) in 30 ml tetrahydrofuran (THF) at 5° C., was added potassium t-butoxide (7.8 g, 0.07 mole) and the mixture was stirred at 5° C. for one hour. To this mixture was added benzyl bromide (7.1 ml, 0.06 mole) in ten minutes, and the mixture stirred at 5° C. for one hour, then at ambient temperature for four hours. This mixture was poured into 100 ml ice-water, stirred for five minutes, then extracted with ethyl acetate. The organic layer was washed with water, then dried (saturated NaCl, anhydrous MgSO4). After filtering, the solvent was evaporated to an oil, 14 g (98%) of N-benzyl-N-(1H-pyrrol-1-yl) carbamic acid ethyl ester. To a solution of N-benzyl-N-(1H-pyrrol-1-yl) carbamic acid ethyl ester (14 g, 0.058 mole) in 15 ml ethylene glycol was added a solution of NaOH (5 g, 0.12 mole) in 10 ml water. After stirring at 120° C. for seven hours, the mixture was poured into 100 ml of iced-water, stirred for five minutes, then extracted with ethyl acetate. The organic layer was washed with water, then dried (saturated NaCl, anhydrous MgSO4). After filtering, the solvent was evaporated to an oil, which was vacuum distilled to give an oil, 7.4 g (74%) of N-benzyl-1H-pyrrol-1-amine, b.p. 85°-125° C./1 mm; m.p. 39°-41° C.

1. waitat ambient temperature for four hours
2. filtrationthe mixture was filtered
3. washthe filtrate was washed with water
4. dry with materialdried (saturated NaCl solution, anhydrous MgSO4)
5. filtrationAfter filtering
6. customthe solvent was evaporated
7. customto give a solid, 17 g (95%), m.p. 60°-61° C.
8. stirringthe mixture was stirred at 5° C. for one hour
9. stirringthe mixture stirred at 5° C. for one hour
10. waitat ambient temperature for four hours
11. stirringstirred for five minutes
12. extractionextracted with ethyl acetate
13. washThe organic layer was washed with water
14. dry with materialdried (saturated NaCl, anhydrous MgSO4)
15. filtrationAfter filtering
16. customthe solvent was evaporated to an oil, 14 g (98%) of N-benzyl-N-(1H-pyrrol-1-yl) carbamic acid ethyl ester
17. stirringAfter stirring at 120° C. for seven hours
18. stirringstirred for five minutes
19. extractionextracted with ethyl acetate
20. washThe organic layer was washed with water
21. dry with materialdried (saturated NaCl, anhydrous MgSO4)
22. filtrationAfter filtering
23. customthe solvent was evaporated to an oil, which
24. distillationdistilled

ORD record

ord-c43ab8cad7c84c67b0c5a30f030bf765

Source dataset

uspto-grants-1991_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05017578