4-Chlorobenzonitrile → 4-(1-pyrrolidinyl)benzonitrile

HRID 1505165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1505165
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1>>[N:10]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Komponenten

3

Edukt 2

HCID 121634-ChlorobenzonitrileHCID 31268Pyrrolidine

Produkt 1

HCID 49612714-(1-pyrrolidinyl)benzonitrileAusbeute 33 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To commercially available 4-chlorobenzonitrile 17 (5 g, 36 mmol) 12 ml of pyrrolidine were added and the reaction was heated at 100° C. for 24 hours in closed vessel. The reaction was evaporated and the residue was dissolved in AcOEt and washed with water and brine. The purification of the crude residue by chromatographic column using AcOEt 1/Petroleum ether 9 as eluant gave 1.68 g of a pale yellow solid. Yield=33% 1HNMR (DMSO, 200 MHz) δ 1.96 (4H, m), 3.28 (4H, m), 6.58 (2H, d, J=9 Hz), 7.51 (2H, d, J=9 Hz)

Aufarbeitung

  1. customThe reaction was evaporated
  2. dissolutionthe residue was dissolved in AcOEt
  3. washwashed with water and brine
  4. customThe purification of the crude residue by chromatographic column

Quellen und Nachweise

ORD-Eintrag
ord-ce869e67e7f94ed1a50fdba6456bb80f
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216975B2

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