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

HRID 1696100노트

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HRID 1696100 반응식
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

참가 물질

5

반응물 3

HCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 114581771-Benzyl-3-oxopiperazine

생성물 1

HCID 114485104-Benzyl-1-phenylpiperazin-2-one수율 50%

시약·촉매·용매 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매

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온도
220 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-b72e5d2a679c47c5b0568e197227c8ad
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163720B2

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