Triethylamine → HCID 178471809, Verbindung

HRID 1664956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1664956
Cl.[CH2:2]([O:4][C:5](=[O:14])[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9][CH2:8]1)[CH3:3].Cl.[N:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([C:26]([Cl:28])=[O:27])=[CH:18][CH:17]=1.C(N(CC)CC)C.CCCCCCC.CCOC(C)=O>ClCCl.CCOC(C)=O>[ClH:28].[CH2:2]([O:4][C:5](=[O:14])[CH2:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([NH:13][C:26]([C:19]2[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:16]=[CH:17][CH:18]=2)=[O:27])[CH2:11][CH2:12]1)[CH3:3]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 12373997Quinoline-4-carbonyl chloride hydrochlorideHCID 21899848Ethylacetate heptaneHCID 178471807HCID 178471807, Verbindung

Produkt 1

HCID 178471809HCID 178471809, VerbindungAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of Trans-(4-Amino-cyclohexyl)-acetic acid ethyl ester hydrochloride (3.63 g, 17 mmol) was solved in dichloromethane (115 mL) and quinoline-4-carbonyl chloride hydrochloride was added (4.184 g, 18 mmol) followed by the slow addition of triethylamine (11.3 mL, 81 mmol) at 0° C. The mixture was stirred at room temperature overnight and the salts obtained were removed by filtration and the filtrate was extracted. The organic layer washed with NaHCO3 and brine. The organic phases were dried and concentrated to obtain 3.8 g of a crude. After a flash chromatography with heptane/AcOEt 4:1 to AcOEt a solid was obtained that was recrystallized with EtOAc and n-heptane to obtain the title compound as a pink solid (2.72 g, 42% yield). MS (m/e): 341.3 (M+H+).

Aufarbeitung

  1. customthe salts obtained
  2. customwere removed by filtration
  3. extractionthe filtrate was extracted
  4. washThe organic layer washed with NaHCO3 and brine
  5. customThe organic phases were dried
  6. concentrationconcentrated
  7. customto obtain 3.8 g of a crude
  8. customthat was recrystallized with EtOAc and n-heptane

Quellen und Nachweise

ORD-Eintrag
ord-bf71ea70275044fd86d18844ebad9903
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039490B2

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