HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Hydroxide → HCID 68683848, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 4-Amino-1-methylpiperidine | HCID 2737531 | — |
| Reactant | 4-Bromo-2,3-difluorobenzoic acid | HCID 19358360 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68683848 | HCID 68683848 | 45% |
Reaction Steps
4-bromo-difluorobenzoic acid (Fluorochem; 3.0 g, 12.66 mol) and HBTU (5.3 g, 13.92 mol) were added to DMF (80 mL), to this was added the required 4-amino-1-methylpiperidine (Fluorochem; 1.59 g, 13.93 mol) and DIPEA (5.0 mL, 27.85 mol), the reaction was stirred for 48 hours, after which the solvent was removed in vacuo to yield a brown gum. The gum was treated with 2.0 M NaOH (50 mL) and extracted with DCM (3×200 ml). Combined extracts were dried and solvent removed in vacuo to yield a dark orange gum which was recrystallised from hot acetonitrile to give the title compound as a white solid (1.9 g, 45%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07709471B2 |
| Source dataset | uspto-grants-2010_05 |
| ORD ID | ord-fc8805cdd2e94dd7af3c2bd5e26a4ccd |
| Source note | uspto-grants-2010_05 |