Triethylamine → 2-((1-Benzyl-4-(4-cyclopropylpiperazin-1-yl)-piperidin-4-yl)methyl)isoindolin-1-one

HRID 45999

Reaktionsgleichung

Reaktionsgleichung von HRID 45999
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:23][NH2:24])([N:14]2[CH2:19][CH2:18][N:17]([CH:20]3[CH2:22][CH2:21]3)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:26][C:27]1[CH:36]=[CH:35][CH:34]=[CH:33][C:28]=1[C:29](OC)=[O:30].C(N(CC)CC)C>C1C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:23][N:24]2[CH2:26][C:27]3[C:28](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:29]2=[O:30])([N:14]2[CH2:19][CH2:18][N:17]([CH:20]3[CH2:22][CH2:21]3)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 57989589(1-Benzyl-4-(4-cyclopropylpiperazin-1-yl)piperidin-4-yl)methanamine

Produkt 1

HCID 579895902-((1-Benzyl-4-(4-cyclopropylpiperazin-1-yl)-piperidin-4-yl)methyl)isoindolin-1-oneAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of (1-benzyl-4-(4-cyclopropylpiperazin-1-yl)piperidin-4-yl)methanamine (see above: synthesis of amine AM12) (1.22 mmol, 1.0 equiv.) and methyl 2-(bromomethyl)benzoate (1.22 mmol, 1.0 equiv.) in benzene (3 ml/mmol) was added triethylamine (2.44 mmol, 2.0 equiv.) and the resulting reaction mixture was refluxed for 25 h. The mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and the organic layer was successively washed with water and brine. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure to give the crude product which was purified by silica gel column chromatography. Yield: 51%.

Aufarbeitung

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 25 h
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe organic layer was successively washed with water and brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-feca17fae52f41da8e02615f3d8018a8
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541573B2

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