Potassium Phosphate, Tribasic → N-(2-(4-benzoylpiperazin-1-yl)-5-nitrophenyl)benzenamine

HRID 1966455ノート

反応式

HRID 1966455 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])[CH2:13][CH2:12]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:17]([N:14]1[CH2:13][CH2:12][N:11]([C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[NH:1][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:16][CH2:15]1)(=[O:18])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 58425640(4-(2-Amino-4-nitrophenyl)piperazin-1-yl)(phenyl)methanone

生成物 1

HCID 46199221N-(2-(4-benzoylpiperazin-1-yl)-5-nitrophenyl)benzenamine収率 20%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

A suspension of (4-(2-amino-4-nitrophenyl)piperazin-1-yl)(phenyl)methanone (0.4 g, 1.2 mmol), copper acetate (0.45 g, 2.5 mmol), potassium phosphate (0.26 g, 1.2 mmol), 18-C-6 (31 mg, 0.12 mmol), 4 Å molecular sieves (1.0 g) and phenylboronic acid and pyridine complex (1.4 g, 3.7 mmol) in 30 ml dry dichloromethane was stirred at room temperature overnight. The reaction was quenched with 20 ml water. The mixture was filtered and extracted with ethyl acetate (3×20 ml), followed by drying over anhydrous sodium sulfate. N-(2-(4-benzoylpiperazin-1-yl)-5-nitrophenyl)benzenamine (0.11 g, 20%) was obtained by flash column chromatograph (50% ethyl acetate in hexanes). 1H NMR (500 MHz, CDCl3) δ (ppm) 3.08 (s, br, 4H), 3.70 (s, br, 4H), 6.43 (s, 1H), 7.12-7.75 (m, 11H), 7.77 (d, J=2.4 Hz, 1H), 8.09 (s, 1H). 13C NMR (125 MHz, CDCl3): δ (ppm) 51.4, 108.9, 115.8, 120.2, 120.7, 123.8, 127.6, 128.5, 129.1, 130.3, 130.5, 135.8, 139.1, 141.1, 145.5, 145.9, 171.1.

後処理

  1. customThe reaction was quenched with 20 ml water
  2. filtrationThe mixture was filtered
  3. extractionextracted with ethyl acetate (3×20 ml)
  4. dry with materialby drying over anhydrous sodium sulfate

出典と根拠

ORDレコード
ord-19b63a587dd74962a329b34d4eda2834
出典データセット
uspto-grants-2013_04
特許番号
US08420640B2

反応ノート

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