Diisopropylethylamine → HCID 59837431, Verbindung

HRID 272934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272934
BrCCCOC1C=CC(C2(C#[N:19])CCCCC2)=CC=1.Cl[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2([C:37]#[N:38])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:27][CH:26]=1.C(N(CC)C(C)C)(C)C.[CH3:48][C:49]1([CH3:54])[CH2:53][CH2:52][CH2:51][NH:50]1>CN1C(=O)CCC1>[NH3:19].[CH3:48][C:49]1([CH3:54])[CH2:53][CH2:52][CH2:51][N:50]1[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2([C:37]#[N:38])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:27][CH:26]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 4147732,2-DimethylpyrrolidineHCID 23091704HCID 23091704, VerbindungHCID 598375041-[4-(3-Bromo-propoxy)-phenyl]-cyclohexanecarbonitrile

Produkt 2

HCID 222AmmoniaHCID 59837431HCID 59837431, VerbindungAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A (1:3) mixture of 1-[4-(3-bromo-propoxy)-phenyl]-cyclohexanecarbonitrile and 1-[4-(3-chloro-propoxy)-phenyl]-cyclohexanecarbonitrile (150 mg, 0.54 mmol), N,N-diisopropylethylamine (188 μL, 1.08 mmol) and 2,2-dimethyl-pyrrolidine (131 mg, 1.08 mmol) in NMP (0.5 mL) was heated at 180° C. in the microwave (Smith Personal Synthesiser) for 600 seconds. The reaction mixture was quenched with water (15 mL) and extracted with ethyl acetate (2×15 mL), dried over Na2SO4, filtered and concentrated in vacuo. The compound was purified by column chromatography on Biotage® silica gel, eluting with dichloromethane:methanol:ammonia, 98:2:0.2 to 95:5:0.5 to give the title compound as a brown oil (31 mg, 17%). 1H NMR (400 MHz, CDCl3) δ7.38 (d, 2H), 6.90 (d, 2H), 4.04 (t, 2H), 2.78 (t, 2H), 2.54 (t, 2H), 2.16-2.12 (m, 2H), 1.94 (pentet, 2H), 1.90-1.64 (m, 11H), 1.20-1.34 (m, 1H), 0.98 (s, 6H); HRMS (ESI+) 341.2588 (M+H)+.

Aufarbeitung

  1. customThe reaction mixture was quenched with water (15 mL)
  2. extractionextracted with ethyl acetate (2×15 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe compound was purified by column chromatography on Biotage® silica gel
  7. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-99f121676a1e4897ae779a4d906ebbbd
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456164B2

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