HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Methylpiperazine → (4-Amino-3-methoxyphenyl)(4-methylpiperazin-1-yl)methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Methylpiperazine | HCID 53167 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2486-69-3 | HCID 288057 | — |
| 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-Amino-3-methoxyphenyl)(4-methylpiperazin-1-yl)methanone | HCID 57416164 | 31.2% |
Reaction Steps
HATU (1179 mg, 3.10 mmol) was added to a solution of 4-amino-3-methoxybenzoic acid (461 mg, 2.76 mmol), DIPEA (1.24 mL, 7.12 mmol) and 1-methylpiperazine (230 mg, 2.30 mmol) in DMF (12 mL) and the reaction mixture was stirred for 18 hours. The reaction was partitioned between EtOAc and water. The organic phase was washed with saturated aqueous NaHCO3 solution, water, dried over Na2SO4 and concentrated in vacuo. The residue was purified by elution through an SCX-2 column to afford the title compound as brown oil (179 mg, 31%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409907B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-e334b8db5e404f698110b4a6bf87a906 |
| Source note | uspto-grants-2016_08 |