HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-(Piperidin-1-yl)aniline → n-[4-(1-Piperidinyl)phenyl]benzo[g]quinolin-4-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-(Piperidin-1-yl)aniline | HCID 413501 | — |
| Reactant | 4-Bromobenzo[g]quinoline | HCID 21712585 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | n-[4-(1-Piperidinyl)phenyl]benzo[g]quinolin-4-amine | HCID 2832014 | 77.5% |
Reaction Steps
4-Bromobenzo[g]quinoline (7a) (140 mg, 0.54 mmol), 4-(I-piperidino)aniline (115 mg, 1.2 equivalents), tris(dibenzylideneacetone)dipalladium (Pd2(dbba)3, (10 mg, 0.02 equivalents), 1,1′-bis(diphenylphosphino)ferrocene (DPPF, 12 mg, 0.04 equivalents) and sodium t-butoxide (73 mg, 1.4 equiv) in 5 mL of dry toluene were refluxed under a nitrogen atmosphere until observed complete by TLC (approximately 1 h). The mixture was concentrated in vacuo and purification by flash chromatography (gradient: 5 50:50:2 to 60:40:2 hexane:EtOAc:Et3N) provided 148 mg of clean N-[4-(1-piperidinyl)phenyl]benzo[g]quinolin-4-amine (8) (77% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06274596B1 |
| Source dataset | uspto-grants-2001_08 |
| ORD ID | ord-4533dcacc6934d90bf2e9b872afc1ac9 |
| Source note | uspto-grants-2001_08 |