Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-(2,5-Xylyl)piperazine | HCID 70542 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 4-(4-Fluoro-2-methyl-phenyl)-piperazine-1,3-dicarboxylic acid 1-tert-butyl ester | HCID 11279174 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68728844 | HCID 68728844 | — |
Reaction Steps
4-(4-fluoro-2-methyl-phenyl)-piperazine-1,3-dicarboxylic acid 1-tert-butyl ester (CAS Reg. No.: [499780-10-8]) (100 mg) in DMF (2.5 mL) was treated with 1-(2,5-dimethylphenyl)piperazine (62 mg), 2-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyl-uronium hexafluoro phosphate (HBTU) (123 mg) and triethylamine (124 μL) at ambient temperature for 5 h. Water was added, the phases were separated and the inorganic phase was extracted with tert-butyl-methyl ether (TBME). The combined organic phases were washed with water and brine, dried (Na2SO4), filtered and evaporated. Purification by chromatography (SiO2, n-heptane/ethyl acetate 2:1) gave 3-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-4-(4-fluoro-2-methyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester as a white solid (143 mg), MS: 511.5 ([M+H]+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08288541B2 |
|---|
| Source dataset | uspto-grants-2012_10 |
|---|
| ORD ID | ord-53447f88905f48d9ae747a06067873e7 |
|---|
| Source note | uspto-grants-2012_10 |
|---|
