Triethylamine → HCID 88117526, Verbindung

HRID 1169427

Reaktionsgleichung

Reaktionsgleichung von HRID 1169427
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][C:14]([CH:18]=O)=[CH:13][C:12]=3[CH:20]=2)=[CH:4][CH:3]=1.[F:21][C:22]([F:33])([F:32])[C:23]([NH:25][CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)CC)C>ClCCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][C:14]([CH2:18][N:29]4[CH2:30][CH2:31][CH:26]([NH:25][C:23](=[O:24])[C:22]([F:21])([F:32])[F:33])[CH2:27][CH2:28]4)=[CH:13][C:12]=3[CH:20]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydride2×HCID 107742532,2,2-trifluoro-N-(piperidin-4-yl)acetamideHCID 229901807-(4-Methylphenyl)-2,3-dihydro-1-benzooxepine-4-carbaldehyde

Produkt 1

HCID 88117526HCID 88117526, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To 7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carbaldehyde (2.0 g) and 4-trifluoroacetamidopiperidine (1.56 g) dissolved in 1,2-dichloroethane (50 ml) was added under ice cooling sodium triacetoxyborohydride (1.8 g), and the resulting mixture was stirred at room temperature overnight under a nitrogen atmosphere. Thereto were added triethylamine (1.1 ml) and sodium triacetoxyborohydride (0.8 g), and the resulting mixture was stirred at room temperature overnight under a nitrogen atmosphere. The reaction mixture was evaporated to remove the solvent, was neutralized with a 1 N aqueous solution of sodium hydrogen carbonate and was extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated solution of sodium chloride, and then was dried with anhydrous magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to remove the solvent to obtain crude crystals (3.0 g). A portion of the crystals was recrystallized from ethyl acetate/hexane to obtain 1-(7-(4-methylphenyl)-2,3-dihydro-1-benzooxepin-4-ylmethy)-4-trifluoroacetamidopiperidine as light yellow crystals.

Aufarbeitung

  1. additionwas added under ice
  2. stirringthe resulting mixture was stirred at room temperature overnight under a nitrogen atmosphere
  3. customThe reaction mixture was evaporated
  4. customto remove the solvent
  5. extractionwas extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialan aqueous saturated solution of sodium chloride, and then was dried with anhydrous magnesium sulfate
  8. customThe resulting organic layer was evaporated under reduced pressure
  9. customto remove the solvent
  10. customto obtain crude crystals (3.0 g)
  11. customA portion of the crystals was recrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-b5956ba290ea41259dbbbe97e3a8840f
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06627651B1

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