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

HRID 1966466Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1966466
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-69ffd6eefbc7440b83f6d062676b7f00
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420640B2

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