Ammonium formate → 4-hydroxy-N-[2-oxo-2-(4-phenylacetyl-piperazin-1-yl)-ethyl]-benzamide

HRID 1177839Notes

Reaction equation

C([O-])=O.[NH4+].C([O:12][C:13]1[CH:39]=[CH:38][C:16]([C:17]([NH:19][CH2:20][C:21](=[O:37])[N:22]2[CH2:27][CH2:26][N:25]([C:28](=[O:36])[CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:24][CH2:23]2)=[O:18])=[CH:15][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[OH:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH:19][CH2:20][C:21](=[O:37])[N:22]2[CH2:23][CH2:24][N:25]([C:28](=[O:36])[CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:26][CH2:27]2)=[O:18])=[CH:38][CH:39]=1

Participants

Conditions

Temperature: 75 °C

Procedure

Ammonium formate (107 mg, 1.6985 mmoles) was added to a mixture of 4-benzyloxy-N-[2-oxo-2-(4-phenylacetyl-piperazin-1-yl)-ethyl]-benzamide (80 mg, 0.17 mmol) in MeOH (15 mL). Pd/C (30 mg in 3 drops of water) was then added and the resulting mixture was refluxed at 75° C. for three hours. The reaction mixture was then filtered through a bed of celite under reduced pressure. The methanol was removed and EtOAc and water were added. The organic layer was extracted, washed with brine, dried over sodium sulphate and concentrated to afford 4-hydroxy-N-[2-oxo-2-(4-phenylacetyl-piperazin-1-yl)-ethyl]-benzamide in 70% yield. LC-MS purity 94.82%. 1H NMR (DMSO-D6): δ 10 (s, 1H), 8.3 (s, 1H), 7.7 (d, 2H), 7.3 (t, 2H), 7.2 (d, 2H), 6.8 (d, 2H), 4.1 (d, 2H), 3.8 (d, 2H), 3.5 (m, 8H).

Workup

filtrationThe reaction mixture was then filtered through a bed of celite under reduced pressure
customThe methanol was removed
additionEtOAc and water were added
extractionThe organic layer was extracted
washwashed with brine
dry with materialdried over sodium sulphate
concentrationconcentrated

Sources & evidence

ORD record: ord-b52a3cc0575645359c5d5e03318d41a0
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842696B2

Reaction notes

Loading…