HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylamine → 3-(4-Chlorophenyl)prop-2-yn-1-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | 1-Chloro-4-iodobenzene | HCID 12510 | — |
| Reactant | Propargylamine | HCID 239041 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-(4-Chlorophenyl)prop-2-yn-1-amine | HCID 58952344 | — |
Reaction Steps
To a solution of 4-chloro iodobenzene (25 g) in 400 mL CH2Cl2 at room temperature was added propargyl amine (13.5 mL), diisopropyl amine (37 mL), CuI (4 g) and Pd(PPh3)2Cl2 (3.7 g). The mixture was stirred overnight at room temperature, diluted with 600 mL EtOAc and filtered through a CELITE pad to remove insoluble materials. The solution washed with water, brine, dried over MgSO4, concentrated and purified by chromatography to provide 14.1 g of 3-(4-chloro-phenyl)-prop-2-ynylamine. MS: m/e 166.1 (MH+)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07897601B2 |
| Source dataset | uspto-grants-2011_03 |
| ORD ID | ord-efc44ef22a6745ec93de5fb19b92ad4c |
| Source note | uspto-grants-2011_03 |