Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium formate | HCID 2723923 | — |
| Reactant | HCID 59559649 | HCID 59559649 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 59559658 | HCID 59559658 | 89% |
Reaction Steps
Ammonium formate (49 mg, 0.77 mmol) was added to a stirred solution of 4-benzyloxy-N-{1-methyl-2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide (42 mg, 0.07 mmol) in MeOH (10 mL). 10% Pd/c (10 mg) was then added and the resulting mixture stirred at room temperature under an inert atmosphere. The reaction mixture was then stirred at reflux temperature for 2 hrs. The mixture was filtered over a bed of celite. The celite was washed with MeOH and the filtrate was concentrated. The residue was dissolved in EtOAc, washed with water, followed by saturated brine solution. The organic layer was dried over sodium sulphate and concentrated in vacuo to afford 28 mg (82% yield) of 4-hydroxy-N-{1-methyl-2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide. LCMS Purity: 95%. 1H NMR (DMSO-d6): δ 7.76 (d, 1H), 7.60 (m, 4H), 7.36 (t, 1H), 7.26 (t, 1H), 6.8 (d, 2H), 5.2 (m, 1H), 4.2 (m, 1H), 3.9-3.4 (m, 8H), 1.4 (dd, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07842696B2 |
|---|
| Source dataset | uspto-grants-2010_11 |
|---|
| ORD ID | ord-c395ffa54d0a42449a71b130fe4f6291 |
|---|
| Source note | uspto-grants-2010_11 |
|---|