Diisopropylethylamine → HCID 54767440, Verbindung

HRID 1690278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1690278
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[C:4]([NH2:16])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:5][CH2:6]2.C(N(CC)C(C)C)(C)C.[CH3:26][O:27][C:28]1[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[C:33]([S:41][CH3:42])[C:29]=1[C:30](Cl)=[O:31]>ClCCl>[CH3:26][O:27][C:28]1[CH:36]=[C:35]([C:37]([F:38])([F:39])[F:40])[CH:34]=[C:33]([S:41][CH3:42])[C:29]=1[C:30]([NH:16][C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:6][CH:7]2[N:2]([CH3:1])[CH:3]1[CH2:9][CH2:8]2)=[O:31]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 58565893(1RS,2RS,5SR)-8-Methyl-2-phenyl-8-aza-bicyclo[3.2.1]oct-2-ylamine2×HCID 59438501HCID 59438501, Verbindung2×

Produkt 1

HCID 54767440HCID 54767440, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of (1RS,2RS,5SR)-8-methyl-2-phenyl-8-aza-bicyclo[3.2.1]oct-2-ylamine (intermediate A1) (670 mg, 3.1 mmol) in dichloromethane (10 ml) under nitrogen at room temperature, was added N,N-diisopropylethylamine (1.23 g, 1.61 ml, 9.29 mmol), followed drop-wise by a solution of 2-methoxy-6-(methylthio)-4-(trifluoromethyl)benzoyl chloride (intermediate B1) (970 mg, 3.41 mmol) in dichloromethane (7 ml). The reaction mixture was stirred at room temperature for 2 hours. The solution was washed once with a 2M sodium carbonate solution. The aqueous layer was extracted once with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude yellow oil (2.04 g), which crystallized in the fridge, was suspended in diethyl ether. The white precipitate was filtered and rinsed with diethyl ether to provide 1.16 g (y: 80.6%) of the title compound as a white solid. MS (m/e): 465.2 (M+H+).

Aufarbeitung

  1. washThe solution was washed once with a 2M sodium carbonate solution
  2. extractionThe aqueous layer was extracted once with dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude yellow oil (2.04 g), which crystallized in the fridge
  7. filtrationThe white precipitate was filtered
  8. washrinsed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-9fe3898022d844759351bfd9fdf80126
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153653B2

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