HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → 4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-3-methyl-piperazin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 3-(3,4-Dichlorophenyl)prop-2-enoic acid | HCID 14548 | — |
| Reactant | 3-methylpiperazin-2-one | HCID 5106600 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-3-methyl-piperazin-2-one | HCID 63079191 | 70% |
Reaction Steps
A solution of 3,4-dichlorocinnamic acid (190 mg, 0.88 mmol), 3-methylpiperazin-2-one (100 mg, 0.88 mmol), 4-methylmorpholine (443 mg, 4.38 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluoro-phosphate (500 mg, 1.31 mmol) in N,N-dimethylformamide (1 ml) was stirred at room temperature for 3 h, then the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2; CH2Cl2/MeOH 95:5) produced the title compound (192 mg, 70%). White solid, MS (ISP)=313.1 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08063042B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-00aac8abf4754bad9e5d4dad4d3a9a4c |
| Source note | uspto-grants-2011_11 |