Triethylamine → 3-(4-Benzoylpiperazin-1-yl)-N-phenylbenzenamine

HRID 1966466노트

반응식

HRID 1966466 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:14]([N:11]1[CH2:10][CH2:9][N:8]([C:4]2[CH:3]=[C:2]([NH:1][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:7]=[CH:6][CH:5]=2)[CH2:13][CH2:12]1)(=[O:15])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 28800116(4-(3-Aminophenyl)piperazin-1-yl)(phenyl)methanone

생성물 1

HCID 584256333-(4-Benzoylpiperazin-1-yl)-N-phenylbenzenamine수율 66%

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매

실험 절차

A suspension of (4-(3-aminophenyl)piperazin-1-yl)(phenyl)methanone (0.5 g, 1.8 mmol), copper acetate (0.65 g, 3.6 mmol), triethylamine (1.7 ml, 12.4 mmol), 4 Å molecular sieves (0.5 g) and phenylboronic acid and pyridine complex (0.70 g, 1.8 mmol) in 30 ml dry dichloromethane was stirred at room temperature overnight. The reaction was quenched with 20 ml water extracted with dichloromethane (3×40 ml), followed by drying over anhydrous sodium sulfate. 3-(4-Benzoylpiperazin-1-yl)-N-phenylbenzenamine (0.42 g, 66%) was obtained by flash column chromatograph (50% ethyl acetate in hexanes). 1H NMR (500 MHz, CDCl3) δ (ppm) 3.20 (d, br, 4H), 3.65 (d, br, 4H), 5.73 (s, 1H), 6.54 (dd, J=8.0, 1.6 Hz, 1H), 6.67 (m, 2H), 6.97 (t, J=7.4 Hz, 1H), 7.11 (dd, J=8.6, 1.0 Hz, 2H), 7.28 (t, J=8.0 Hz, 1H), 7.44 (m, 2H), 7.48 (m, 5H). 13C NMR (125 MHz, CDCl3): δ (ppm) 50.0, 50.1, 50.3, 106.5, 110.0, 110.7, 118.6, 121.6, 127.6, 129.0, 129.8, 130.3, 130.5, 136.1, 143.5, 144.7, 152.6, 170.9.

후처리

  1. customThe reaction was quenched with 20 ml water
  2. extractionextracted with dichloromethane (3×40 ml)
  3. dry with materialby drying over anhydrous sodium sulfate

출처 및 근거

ORD 기록
ord-69ffd6eefbc7440b83f6d062676b7f00
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420640B2

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