Sodium Iodide → 6-Bromo-2-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinoline

HRID 1713094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713094
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2.Cl[CH:14]1[CH2:19][N:18]([CH:20]2[CH2:23][CH2:22][CH2:21]2)[CH2:17][CH2:16][NH:15]1.[C:24](N)(=[O:26])[CH3:25].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C.O>[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([CH2:25][C:24]([N:15]1[CH2:16][CH2:17][N:18]([CH:20]3[CH2:23][CH2:22][CH2:21]3)[CH2:19][CH2:14]1)=[O:26])[CH2:7][CH2:6]2

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 225702166-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 668779022-Chloro-(4-cyclobutyl-piperazine) acetamide

Produkt 1

HCID 574205706-Bromo-2-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred solution of 6-bromo-1,2,3,4-tetrahydro-isoquinoline hydrochloride (3.09 g, 12.4 mmol) in acetonitrile (50.0 ml) is added 2-chloro-(4-cyclobutyl-piperazine)-acetamide (2.69 mg, 12.4 mmol, 1.0 eq.), K2CO3 (5.14 g, 37.3 mmol, 3.0 eq.), and NaI (400 mg). The resulting mixture is stirred at rt overnight. Water (40.0 ml) is added to quench the reaction, and then the acetonitrile is evaporated. The residue is extracted with DCM (40 ml×3). The combined organic phase is dried over sodium sulfate, and the solvent is removed under reduced pressure to give a residue that is purified by flash silica gel chromatography (EtOAc/4% TEA) to give the title compound. MS (+VE) m/z 392.2 (M++1).

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. customthe acetonitrile is evaporated
  4. extractionThe residue is extracted with DCM (40 ml×3)
  5. dry with materialThe combined organic phase is dried over sodium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customto give a residue that
  8. customis purified by flash silica gel chromatography (EtOAc/4% TEA)

Quellen und Nachweise

ORD-Eintrag
ord-f4e9ceaaaaa54b9a966ecca8ec436657
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795262B2

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