HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Cis-3,5-dimethyl-1-(4-nitro-phenylmethanesulfonyl)-piperazine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (4-Nitrophenyl)methanesulfonyl chloride | HCID 2794642 | — |
| Reactant | rel-(2R,6S)-2,6-dimethylpiperazine | HCID 6950261 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Cis-3,5-dimethyl-1-(4-nitro-phenylmethanesulfonyl)-piperazine | HCID 58994592 | 90% |
Reaction Steps
A solution of 250 mg (1.06 mmol) of 4-nitrophenylmethanesulfonyl chloride and 133 mg (1.17 mmol) of cis-2,6-dimethylpiperazine in CH2Cl2 (10 mL) was treated with 325 μL (2.33 mmol) of triethylamine at RT for 20 min. The mixture was diluted with CH2Cl2 (15 mL) and washed with water (1×15 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to afford 298 mg (90%) of the title compound as an off-white solid: 1H-NMR (CDCl3; 400 MHz): δ 8.25 (d, 2H, J=8.8 Hz), 7.87 (d, 2H, J=8.8 Hz), 4.24 (s, 1H), 3.59-3.53 (m, 2H), 2.92-2.82 (m, 2H), 2.30-2.23 (m, 2H), 1.04 (d, 6H, J=6.0 Hz). Mass spectrum (ESI, m/z): Calcd. for C13H19N3O4S, 314.1 (M+H). found 314.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09221797B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-dbb4bc8cdb0e469a964cf164d335bb0b |
| Source note | uspto-grants-2015_12 |