Ammonia → HCID 178424855, Verbindung

HRID 2252839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2252839
[CH:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([NH2:10])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].Cl[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[C:14](CCC2C=NC(C)=CC=2)[N:13]=1.[NH3:31].O>CCOC(C)=O>[CH:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH2:2][CH2:1][C:4]3[CH:9]=[N:31][C:7]([CH3:8])=[CH:6][CH:5]=3)=[CH:14][N:13]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 962WaterHCID 86594687HCID 86594687, VerbindungHCID 178448118HCID 178448118, Verbindung

Produkt 1

HCID 178424855HCID 178424855, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under a N2 atmosphere, 600 mg (4.25 mmol) of trans-4-isopropyl-cyclo-hexylamine [for preparation see Arzneim. Forsch. 19 (1969), 140] and 120 mg (0.424 mmol) of 1-chloro[2-(6-methyl-pyridin-3-yl)-ethyl]-isoquinoline are heated to 140° C. in an ampulla for 10 h. The reaction mixture is suspended in EtOAc, and mixed with 0.25 ml of NH3 solution (25%) and water. The separated aqueous phase is extracted twice more with EtOAc, the organic phases washed with water and brine, dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2; hexane/EtOAc 1:1) yields trans 1-(4-isopropyl-cyclohexylamino)-4-[2-(6-methyl-pyridin-3-yl)-ethyl]-isoquinoline; 1H NMR (DMSO-d6) δ 8.27 (m, 2H), 7.88 (d, 1H), 7.65 (t, 1H), 7.60 (s, 1H), 7.54 (m, 1H), 7.14 (d, 1H), 6.84 (d, 1H), 3.88 (m, 1H), 3.00 (m, 2H), 2.84 (m, 2H), 2.40 (s, 3H), 2.00 (m, 2H), 1.71 (m, 2H), 1.5-1.0 (m, 6H), 0.86 (d, 6H).

Aufarbeitung

  1. extractionThe separated aqueous phase is extracted twice more with EtOAc
  2. washthe organic phases washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-04dff1b9a1384767a1378cbfde1eedec
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07323474B2

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