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

HRID 1966455노트

반응식

HRID 1966455 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-19b63a587dd74962a329b34d4eda2834
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420640B2

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