HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → (4-Bromo-2-methylphenyl)(2,5-dihydro-1H-pyrrol-1-yl)methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 3-Pyrroline | HCID 66059 | — |
| Reactant | 4-Bromo-2-methylbenzoic acid | HCID 99570 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (4-Bromo-2-methylphenyl)(2,5-dihydro-1H-pyrrol-1-yl)methanone | HCID 22600480 | — |
Reaction Steps
25.0 g (0.12 mol) of 4-bromo-2-methylbenzoic acid is dissolved in 250 mL of dimethylformamide and after the addition of 41.7 g (0.13 mol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU), 14.3 mL (0.13 mol) of N-methylmorpholine and 9.6 mL (0.12 mol) of 2,5-dihydropyrrole, the mixture is stirred for 16 hours at ambient temperature. Then it is poured onto ice water and extracted with ethyl acetate. The combined organic extracts are washed with sodium hydrogen carbonate solution, dried over sodium sulfate and concentrated by evaporation. Yield: 31.6 g (97% of theory); Rf value: 0.45 (silica gel; dichloromethane/ethanol=19:1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07326791B2 |
| Source dataset | uspto-grants-2008_02 |
| ORD ID | ord-13068a93f2ec4ec2ac10d0c3f94f8be7 |
| Source note | uspto-grants-2008_02 |