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

HRID 1696100ノート

反応式

HRID 1696100 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 114485104-Benzyl-1-phenylpiperazin-2-one収率 50%

試薬・触媒・溶媒 1

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

反応条件

温度
220 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b72e5d2a679c47c5b0568e197227c8ad
出典データセット
uspto-grants-2012_04
特許番号
US08163720B2

反応ノート

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