Dimethylformamide → 4-{4-[3-(2,5-Dimethylpyrrolidin-1-yl)propoxy]phenyl}-tetra-hydropyran-4-carbonitrile

HRID 272901Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272901
N1(CCC[O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:22]#[N:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)CCCC1.Cl[CH2:25][CH2:26][CH2:27][N:28]1[C@@H:32]([CH3:33])[CH2:31][CH2:30][C@@H:29]1[CH3:34].CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>C(OCC)(=O)C>[CH3:34][CH:29]1[CH2:30][CH2:31][CH:32]([CH3:33])[N:28]1[CH2:27][CH2:26][CH2:25][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:22]#[N:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 598373944-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrileHCID 685770241-(3-Chloro-propyl)-2,5-trans-dimethyl-pyrrolidine

Produkt 1

HCID 685779264-{4-[3-(2,5-Dimethylpyrrolidin-1-yl)propoxy]phenyl}-tetra-hydropyran-4-carbonitrileAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile (318 mg, 1.56 mmol), 1-(3-chloro-propyl)-2,5-trans-dimethyl-pyrrolidine (250 mg, 1.42 mmol), DMF (5 ml) and K2CO3 (785 mg, 5.70 mmol) were reacted together according to general procedure E. The crude was dissolved in ethyl acetate (20 ml), washed with brine (2×10 ml), dried over MgSO4, filtered and concentrated in vacuo to give the title compound (200 mg, 56%) as a light brown solid. 1H NMR (400 MHz, CDCl3), δ 7.37 (d, 2H), 6.93 (d, 2H), 4.13-3.97 (m, 4H), 3.89 (td, 2H), 3.14-2.98 (m, 2H), 2.76 (m, 1H), 2.55 (m, 1H), 2.16-1.88 (m, 8H), 1.46-1.30 (m, 2H), 0.97 (d, 6H).

Aufarbeitung

  1. washwashed with brine (2×10 ml)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-06c3f9326e7d4a59ab341a7904b977df
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456164B2

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