HuagongsheHuagongshe Chemistry Print Report · For research reference only
Butylamine → HCID 86627340, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Butylamine | HCID 8007 | — |
| Reactant | 1-Hexyne | HCID 12732 | — |
| Reactant | tert-Butyl 4-(bromomethylidene)piperidine-1-carboxylate | HCID 45489892 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Product | HCID 86627340 | HCID 86627340 | 77.7% |
Reaction Steps
A mixture of palladium tetrakis(triphenylphosphine) (21 mg, 0.018 mmol), butylamine (2.5 mL) and Compound 49a (200 mg, 0.724 mmol) were stirred at room temperature for 45 minutes. Copper iodide (10.3 mg, 0.05 mmol) was then added, followed by hex-1-yne (41.6 μL, 0.362 mmol). The solution was heated for 3-5 hours at 70° C. till change in colour to depth blue. The reaction was quenched with ammonium chloride, extracted with diethyl ether, washed with brine, dried over magnesium sulphate, filtered, concentrated to dryness and purified by preparative HPLC-MS e affording the title product (78 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08518916B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-02db806b209e4512a310c3b5f4ceddec |
| Source note | uspto-grants-2013_08 |