Cyclohexanecarboxaldehyde → (5-[cyclohexylmethyl-(2-pyridin-3-ylethyl)amino]pentyloxy}-1-methyl-1H-quinolin-2-one dihydrochloride

HRID 69003

Reaktionsgleichung

Reaktionsgleichung von HRID 69003
[ClH:1].Cl.C[N:4]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]1=O.[CH:30]1([CH:36]=O)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.[Na].[C:39](=[O:42])([O-])O.[Na+].C(O)C.Cl>C(OCC)(=O)C.C(O)C.ClCCCl.C(N(CC)CC)C>[ClH:1].[ClH:1].[CH:30]1([CH2:36][N:20]([CH2:21][CH2:22][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][O:14][C:10]2[C:39](=[O:42])[N:4]([CH3:5])[C:13]3[C:8]([CH:9]=2)=[CH:7][CH:6]=[CH:11][CH:12]=3)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Komponenten

10

Edukt 5

HCID 16275CyclohexanecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 21887872Ethanol hydrochlorideHCID 669605681-methyl-6-[5-(2-pyridin-3-ylethylamino)pentyloxy]-1H-quinolin-2-one dihydrochloride

Produkt 1

HCID 86670485(5-[cyclohexylmethyl-(2-pyridin-3-ylethyl)amino]pentyloxy}-1-methyl-1H-quinolin-2-one dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 111,2-DichloroethaneLösungsmittelHCID 702EthanolLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Triethylamine (0.15 ml) was added to a 1,2-dichloroethane solution (2.5 ml) of 1-methyl-6-[5-(2-pyridin-3-ylethylamino)pentyloxy]-1H-quinolin-2-one dihydrochloride (219 mg). The mixture was stirred at room temperature for 30 minutes. Cyclohexane carboxaldehyde (0.073 ml) and sodium triacetoxyborohydrate (159 mg) were added thereto, and the mixture was stirred at room temperature overnight. A saturated sodium hydrogencarbonate aqueous solution was added to the reaction mixture, followed by extraction using dichloromethane. The organic layer was dried with anhydrous sodium sulfate, and condensed under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1). The purified product was condensed under reduced pressure. A 1N-hydrogen chloride ethanol solution (1.0 ml) was added to an ethanol solution (20 ml) of the residue, which was stirred at room temperature. The reaction mixture was condensed under reduced pressure and ethyl acetate was added to the residue. The precipitated insoluble matter was separated, washed with ethyl acetate, and dried to give the title compound (100 mg) as a pale yellow powder.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionfollowed by extraction
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate, and condensed under reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1)
  5. customcondensed under reduced pressure
  6. stirringwas stirred at room temperature
  7. additionwas added to the residue
  8. customThe precipitated insoluble matter was separated
  9. washwashed with ethyl acetate
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7fe99b646ddc4c14942d498c8193c493
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822453B2

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