HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Cyclopropyl-{6-[1-(4-fluoro-phenyl)-1h-indol-5-yloxy]-hexyl}-methyl-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 5-(6-Bromo-hexyloxy)-1-(4-fluoro-phenyl)-1H-indole | HCID 11749612 | — |
| Product | Cyclopropyl-{6-[1-(4-fluoro-phenyl)-1h-indol-5-yloxy]-hexyl}-methyl-amine | HCID 18679440 | 73% |
Reaction Steps
195 mg (0.5 mmol) 5-(6-Bromo-hexyloxy)-1-(4-fluoro-phenyl)-1H-indole in 2.5 ml DMF were treated with 185 mg (1 mmol) cyclopropyl-methyl amine·CF3CO2H and 96 mg (2 mmol, 50% in mineral oil) NaH at RT for 2 h and at 60° C. for 3 h. At RT, ether and water were added and the inorganic phase was extracted with ether. The combined organic phases were washed with water, dried over Na2SO4 and evaporated. Purification on silica gel with hexane/ether 1:1 yielded 140 mg (73%) Cyclopropyl-{6-[1-(4-fluoro-phenyl)-1H-indol-5-yloxy]-hexyl}-methyl-amine as light yellow oil, MS: 381 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06503907B2 |
| Source dataset | uspto-grants-2003_01 |
| ORD ID | ord-938d48b6940f48ac8d2b9d98ce7707bd |
| Source note | uspto-grants-2003_01 |