Diisopropylethylamine → Benzo[d]isoxazol-3-yl(4-(4-chlorophenoxy)piperidin-1-yl)methanone

HRID 2170853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2170853
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[O:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[C:26]([C:33](Cl)=[O:34])=[N:25]1>ClCCl.C(OCC)(=O)C>[O:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[C:26]([C:33]([N:10]2[CH2:9][CH2:8][CH:7]([O:6][C:5]3[CH:13]=[CH:14][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:12][CH2:11]2)=[O:34])=[N:25]1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 51998894-(4-Chlorophenoxy)piperidineHCID 10419807Benzo[d]isoxazole-3-carbonyl Chloride

Produkt 1

HCID 67168793Benzo[d]isoxazol-3-yl(4-(4-chlorophenoxy)piperidin-1-yl)methanoneAusbeute 38,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-(4-chlorophenoxy)piperidine (26 mg, 0.12 mmol), and N,N-diisopropylethylamine (0.086 mL, 0.49 mmol) in dichloromethane (0.5 mL) was added dropwise a solution of benzo[d]isoxazole-3-carbonyl chloride (22 mg, 0.12 mmol) in dichloromethane (0.5 mL) at room temperature. The reaction mixture was stirred at room temperature for 1 hour. The mixture was diluted with ethyl acetate (3 mL) and washed with water (1.5 mL). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate) and then preparative LC-MS to give 16.3 mg (37% yield) of the title compound.

Aufarbeitung

  1. washwashed with water (1.5 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-36bcb924382c4a8db4d73e601405ff10
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051296B2

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