Bromobenzene → 4-Benzyl-1-phenylpiperazin-2-one

HRID 1715903Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([N:15]1[CH2:20][CH2:19][NH:18][C:17](=[O:21])[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu]I>[CH2:8]([N:15]1[CH2:20][CH2:19][N:18]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:17](=[O:21])[CH2:16]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 220 °C

Procedure

To a 25 mL microwave vessel was added 4-bromobenzene (6.1 g, 39.0 mmol), 4-benzylpiperazin-2-one (5.0 g, 36.3 mmol), potassium carbonate (3.6 g, 26.3 mmol), and copper(I) iodide (500 mg, 2.6 mmol). The reaction vessel was sealed and purged with nitrogen. Anhydrous NMP (8.0 mL) was added via syringe. The vessel was heated via microwave at 220° C. for 40 minutes. The mixture was filtered through a bed of celite followed by CH2Cl2 (20 mL). The filtrate was purified via silica gel chromatography using 2% MeOH in CH2Cl2 to obtain the desired piperazinone as a white solid (3.4 g, 12.7 mmol, 50% yield). 1H NMR (400 MHz, CDCl3) δ 7.42-7.24 (m, 10H), 3.69 (t, J=5.4 Hz, 1H), 3.63 (s, 1H), 3.40-3.31 (m, 2H), 2.84 (s, 1H), 2.81 (t, J=5.2 Hz, 1H). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=267.3; tR=1.63 min.

Workup

customThe reaction vessel was sealed
custompurged with nitrogen
additionAnhydrous NMP (8.0 mL) was added via syringe
filtrationThe mixture was filtered through a bed of celite
customThe filtrate was purified via silica gel chromatography

Sources & evidence

ORD record: ord-3b1d49de01df443fa391d72b3f9401d4
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799822B2

Reaction notes

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