Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-Chloro-4-iodobenzene | HCID 12510 | — |
| Reactant | Allyl-[4-(2,3-dihydro-1H-indol-5-yloxy)-butyl]-methyl-amine | HCID 21966572 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 18679562 | HCID 18679562 | 20.3% |
Reaction Steps
260 mg (1 mmol) Allyl-[4-(2,3-dihydro-1H-indol-5-yloxy)-butyl]-methyl-amine in 2.5 ml DMSO were treated with 280 mg (2 mmol) powdered K2CO3 and 480 mg (2 mmol) 1-chloro-4-iodobenzene at 130° C. for 1 h. 19.1 mg (0.1 mmol) CuI were added and the mixture was stirred for additional 2 h at 130° C. At RT, water and ether were added, and the organic phase was washed with water, dried over Na2SO4. Column chromatography on silica gel with CH2Cl2/MeOH 19:1 yielded 75 mg (20%) Allyl-{4-[1-(4-chloro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-amine as orange oil, MS: 369 (MH+, 1Cl).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06503907B2 |
|---|
| Source dataset | uspto-grants-2003_01 |
|---|
| ORD ID | ord-87400874405e4e1fab74b2a102e79f41 |
|---|
| Source note | uspto-grants-2003_01 |
|---|
