HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 1-((3-Bromofuran-2-yl)methyl)-4-methylpiperazine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Methylpiperazine dihydrochloride | HCID 2734715 | — |
| Reactant | 3-Bromo-2-furaldehyde | HCID 3367271 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 1-((3-Bromofuran-2-yl)methyl)-4-methylpiperazine | HCID 71066091 | 78% |
Reaction Steps
To a solution of 3-bromofuran-2-carbaldehyde (500 mg, 2.85 mmol), 1-methylpiperazine dihydrochloride (986 mg, 5.71 mmol) and triethylamine (1.5 mL, 11.4 mmol) in CH2Cl2 (10 mL) was added sodium triacetoxyborohydride (1.2 g, 5.71 mmol). The mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with EtOAc (100 mL). The organic phase was washed with aqueous NaHCO3 and brine then dried (MgSO4), filtered and concentrated to dryness. The residue was purified by column chromatography (silica, 0-10% MeOH in CH2Cl2) to afford the sub-title compound (570 mg, 78%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08324264B1 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-c363176ef2d44bd8967264a4ecbacfe4 |
| Source note | uspto-grants-2012_12 |