HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → HCID 71239589, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Ammonium Hydroxide | HCID 14923 | — |
| Reactant | 1-Methylpiperazine | HCID 53167 | — |
| Reactant | 3-Ethynylbenzaldehyde | HCID 2771644 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 71239589 | HCID 71239589 | 38% |
Reaction Steps
3-Ethynylbenzaldehyde (90 mg, 0.69 mmol) and 1-methylpiperazine (92 μL, 0.828 mmol) in 1,4-dioxane (2.6 mL), under a nitrogen atmosphere, at room temperature were treated first with TFA (128 μL, 1.66 mmol), then with sodium triacetoxyborohydride (210 mg, 1.035 mmol) and stirred for 5 h. EtOAc was added to the reaction mixture (20 mL) and 10% NH4OH (15 mL) was added drop wise. The organic layer was separated, dried over sodium sulfate and evaporated. Purification of the crude by flash chromatography over silica gel (DCM/7N NH3 in MeOH 9/1) afforded the title compound (56 mg, 38%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08912200B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-a7e43f372e764aad983d7ebf353b6413 |
| Source note | uspto-grants-2014_12 |