HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-4-phenoxy-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1-Benzylpiperazine | HCID 75994 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-[(4-Phenoxyphenyl)formamido]acetic acid | HCID 2404831 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-[2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-4-phenoxy-benzamide | HCID 27671405 | 58% |
Reaction Steps
DIPEA (0.114 mL, 0.66 mmol) was added drop wise to (4-phenoxy-benzoylamino)-acetic acid (60 mg, 0.22 mmol) in DMF (5 mL). EDCI (106 mg, 0.55 mmol) and HOBT (35 mg, 0.27 mmol) were then added, and after 10 mins, 1-Benzyl-piperazine (46 mg, 0.27 mmol) was added. The resulting mixture was stirred at room temperature overnight. Water was added, and the resulting solid was isolated by filtration under reduced pressure to afford N-[2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-4-phenoxy-benzamide in 58% yield. LC-MS purity: 99%, 1H NMR (DMSO-D6): δ 8.5 (t, 1H), 7.9 (d, 2H), 7.5 (t, 2H), 7.3 (m, 7H), 7.1 (m, 4H), 4.1 (d, 2H), 3.6 (s, 2H), 3.5 (m, 4H), 2.4 (m, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07842696B2 |
| Source dataset | uspto-grants-2010_11 |
| ORD ID | ord-def73861ad794c1085fffa04b57b9c44 |
| Source note | uspto-grants-2010_11 |