Diisopropylethylamine → HCID 59837440, Verbindung

HRID 272932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272932
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:18]#[N:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1.ClCCCOC1C=CC(C2(C#N)CCCCC2)=CC=1.C(N(CC)C(C)C)(C)C.[CH3:48][O:49][C@H:50]1[CH2:54][CH2:53][NH:52][CH2:51]1>CN1C(=O)CCC1>[CH3:48][O:49][C@H:50]1[CH2:54][CH2:53][N:52]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3([C:18]#[N:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)=[CH:8][CH:7]=2)[CH2:51]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 23091704HCID 23091704, VerbindungHCID 26191850(S)-3-MethoxypyrrolidineHCID 598375041-[4-(3-Bromo-propoxy)-phenyl]-cyclohexanecarbonitrile

Produkt 1

HCID 59837440HCID 59837440, VerbindungAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A (1:3) mixture of 1-[4-(3-bromo-propoxy)-phenyl]-cyclohexanecarbonitrile and 1-[4-(3-chloro-propoxy)-phenyl]-cyclohexanecarbonitrile (200 mg, 0.72 mmol), N,N-diisopropylethylamine (251 μL, 1.44 mmol) and (S)-3-methoxy-pyrrolidine (198 mg, 1.96 mmol) in NMP (0.5 mL) was heated at 160° C. in the microwave (Smith Personal Synthesiser) for 400 seconds. The reaction mixture was quenched with water (10 mL) and extracted with dichloromethane (2×10 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, 97:3:0.3 to 95:5:0.5. to give the product as a clear oil (102 mg, 41%). 1H NMR (400 MHz, CDCl3) δ7.36 (d, 2H), 6.90 (d, 2H), 4.02 (t, 2H), 3.96-3.88 (m, 1H), 3.28 (s, 3H), 2.86-2.52 (m, 6H), 2.18-1.96 (m, 5H), 1.88-1.66 (m, 8H), 1.38-1.16 (m, 1H); LCMS (APCI+) 343 (M+H)+.

Aufarbeitung

  1. customThe reaction mixture was quenched with water (10 mL)
  2. extractionextracted with dichloromethane (2×10 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-0e195e8963c44d9785789337582c9a86
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456164B2

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