HuagongsheHuagongshe Chemistry Print Report · For research reference only
Propylamine → 4,5-Dihydro-3-oxo-4-(2-propenyloxy)-N-propyl-2,5-methano-2H-1,2,4-benzotriazepine-1(3H)-acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Propylamine | HCID 7852 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | HCID 69220293 | HCID 69220293 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethylacetate heptane | HCID 21899848 | — |
| Product | 4,5-Dihydro-3-oxo-4-(2-propenyloxy)-N-propyl-2,5-methano-2H-1,2,4-benzotriazepine-1(3H)-acetamide | HCID 69221663 | 38% |
Reaction Steps
480 mg of the acid obtained in Example 25 are dissolved in 5 ml of DMF. 336.5 mg of 1-hydroxybenzotriazole hydrate and then 350 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride are added at 0° C. After 20 min at 0° C., 107.9 g of propylamine are added and then the mixture is left at 0° C. for 20 min. The reaction medium is treated with a heptane/AcOEt (1:2) mixture and NaH2SO4 (1M aqueous solution). After extracting with AcOEt and then washing the organic phase with water, the organic phase is dried over MgSO4 and the solvent is evaporated. The residue is chromatographed on silica (eluent: CH2Cl2; 6% acetone). 207 mg of the expected product (38%) are isolated.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07365071B2 |
| Source dataset | uspto-grants-2008_04 |
| ORD ID | ord-4b8cbeb0d0594f4ebd983628f397706a |
| Source note | uspto-grants-2008_04 |