Chloroacetonitrile → 2-(4-(Quinazolin-4-yl)piperazin-1-yl)acetonitrile

HRID 600472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600472
[N:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:17][CH2:18][N:19](CC)CC.ClCC#N>C1COCC1>[N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([N:1]2[CH2:6][CH2:5][N:4]([CH2:17][C:18]#[N:19])[CH2:3][CH2:2]2)=[N:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 18585334-Piperazin-1-ylquinazoline

Produkt 1

HCID 552058602-(4-(Quinazolin-4-yl)piperazin-1-yl)acetonitrileAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-(piperazin-1-yl)quinazoline (1.8 g, 8.3 mmol) in THF (50 mL) was added NEt3 (20 mL, 150 mmol) and chloroacetonitrile (12 mL, 190 mmol) and the reaction was stirred 16 h. The reaction mixture was quenched with 50% saturated aqueous NaHCO3 and extracted with EtOAc (3×200 mL). The combined organics were purified by silica gel chromatography (50% EtOAc/hexanes to 80% EtOAc/hexanes) to yield 55 (1.6 g, 6.1 mmol, 73%) as an viscous yellow oil. 1H NMR: (500 MHz, CDCl3) δ 8.74 (s, 1H), 8.06 (d, J=8.6 Hz, 1H), 7.90 (d, J=8.5 Hz, 1H), 7.82-7.55 (m, 1H), 7.54-7.50 (m, 1H), 3.94-3.88 (m, 4H), 3.63 (s, 2H), 2.86-2.81 (m, 4H); LC/MS: (ES+) m/z (M+H)+=254; HPLC Rt=0.71 min., column O.

Aufarbeitung

  1. customThe reaction mixture was quenched with 50% saturated aqueous NaHCO3
  2. extractionextracted with EtOAc (3×200 mL)
  3. customThe combined organics were purified by silica gel chromatography (50% EtOAc/hexanes to 80% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-70497f208cad4104bc1f2bbf2ae09378
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902204B2

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