HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → N-(3,4-Dichlorophenyl)-4-[(3R)-piperidin-3-ylmethyl]piperazine-1-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | tert-Butyl (3S)-3-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)methyl]piperidine-1-carboxylate | HCID 57656932 | — |
| Solvent | Water | HCID 962 | — |
| Product | N-(3,4-Dichlorophenyl)-4-[(3R)-piperidin-3-ylmethyl]piperazine-1-carboxamide | HCID 57656731 | 67.4% |
Reaction Steps
tert-Butyl (3S)-3-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)methyl]piperidine-1-carboxylate (1 g), trifluoroacetic acid (10 ml) and dichloromethane (20 ml) were stirred at room temperature for one hour. The solvent was removed in vacuo to yield a dark brown oil. Water (20 ml) was added to this giving a milky solution and this was then basified to ˜pH 6 by addition of solid NaHCO3. This left a milky solution which was diluted with water (˜50 ml) before extracting with ethyl acetate (3×75 ml). The combined organics were washed with brine (˜100 ml) and separated then dried (MgSO4) before removing solvent in vacuo to yield the title compound (531 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08710224B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-248b5b6cf3164492a26446a174887cf2 |
| Source note | uspto-grants-2014_04 |