Sodium Hydroxide → N-(1-cyclohexylmethylpiperidin-4-yl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide

HRID 1169396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1169396
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([C:10]2[CH2:11][CH2:12][O:13][C:14]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=4)=[CH:17][C:15]=3[CH:16]=2)=[O:9])[CH2:3][CH2:2]1.[CH:28]1([CH:34]=O)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl>[CH:28]1([CH2:34][N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8]([C:10]3[CH2:11][CH2:12][O:13][C:14]4[CH:20]=[CH:19][C:18]([C:21]5[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=5)=[CH:17][C:15]=4[CH:16]=3)=[O:9])[CH2:5][CH2:6]2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 16275CyclohexanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 22990182N-(4-piperidinyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide

Produkt 1

HCID 22990127N-(1-cyclohexylmethylpiperidin-4-yl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamideAusbeute 68,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To N-(4-piperidinyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide (0.15 g) and cyclohexane carbaldehyde (0.056 g) dissolved in 1,2-dichloroethane (10 ml) was added sodium triacetoxyborohydride (0.13 g) under ice cooling, and the resulting mixture was stirred at room temperature overnight under a nitrogen atmosphere. The reaction mixture was neutralized with a 1 N aqueous solution of sodium hydroxide, was then concentrated and was extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated solution of sodium chloride, and was then dried with anhydrous magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to remove the solvent to obtain crude crystals. The crude crystals were recrystallized from ethyl acetate/hexane to obtain N-(1-cyclohexylmethylpiperidin-4-yl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide (compound 55) (0.13 g) as colorless prisms.

Aufarbeitung

  1. concentrationwas then concentrated
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialan aqueous saturated solution of sodium chloride, and was then dried with anhydrous magnesium sulfate
  5. customThe resulting organic layer was evaporated under reduced pressure
  6. customto remove the solvent
  7. customto obtain crude crystals
  8. customThe crude crystals were recrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-cfb5cac5cc874539a7ea79aeeb202377
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06627651B1

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