HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Bromo-2-fluorobenzene → N-[(2-fluorophenyl)methyl]-1-methylpiperidin-4-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Bromo-2-fluorobenzene | HCID 61259 | — |
| Reactant | 1-Methyl-4-(methylamino)piperidine | HCID 566323 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | N-[(2-fluorophenyl)methyl]-1-methylpiperidin-4-amine | HCID 781972 | 24.8% |
Reaction Steps
Mix 1-bromo-2-fluorobenzene (3.50 g), 1-methyl-4-(methylamino)piperidine (2.56 g), Pd2(dba)3 (0.366 g), racemic BINAP (0.498 g) and sodium t-butoxide (2.70 g) in toluene (40 mL) and heat at reflux for two days. Filter through a Celite® bed, partition between dichloromethane and saturated aqueous NaCl, dry over anhydrous sodium sulfate, evaporate and purify on a silica gel column (35 g), using a gradient of dichloromethane-2M NH3 in methanol to give 1.1 g of the title intermediate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07803813B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-1bcfddb5aa554336b4ded4496f106db9 |
| Source note | uspto-grants-2010_09 |