Potassium Carbonate → 4-[4-(2-Methyl-3-pyrrolidin-1-ylpropoxy)phenyl]-tetrahydro-pyran-4-carbonitrile

HRID 272913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272913
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[CH2:17][CH:18]([CH3:25])[CH2:19][N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:17][CH:18]([CH2:19][N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)[CH2:25][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 225682631-(3-Chloro-2-methyl-propyl)-pyrrolidineHCID 230916094-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile

Produkt 1

HCID 598375434-[4-(2-Methyl-3-pyrrolidin-1-ylpropoxy)phenyl]-tetrahydro-pyran-4-carbonitrileAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile (790 mg, 3.87 mmol), 1-(3-chloro-2-methyl-propyl)-pyrrolidine (500 mg, 3.10 mmol), DMF (5 ml) and K2CO3 (2.14 g, 15.50 mmol) were reacted together according to general procedure E. The organic phase was washed with 2M NaOH (3×20 ml), water (2×20 ml), dried over MgSO4, fitered and concentrated in vacuo at 35° C. to provide the title compound (979 mg, 96%) as a yellow solid. 1H NMR (400 MHz, CDCl3), δ 7.37 (d, 2H), 6.95 (d, 2H), 4.11-4.03 (m, 2H), 4.02 (dd, 1H), 3.89 (td, 2H), 3.77 (dd, 1H), 2.60-2.42 (m, 5H), 2.32 (dd, 1H), 2.22-1.99 (m, 5H), 1.82-1.72 (m, 4H), 1.07 (d, 3H).

Aufarbeitung

  1. washThe organic phase was washed with 2M NaOH (3×20 ml), water (2×20 ml)
  2. dry with materialdried over MgSO4
  3. concentrationfitered and concentrated in vacuo at 35° C.

Quellen und Nachweise

ORD-Eintrag
ord-824472b7077a4822b65628bb2103b3ec
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456164B2

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