1-Phenylcyclopropanecarbonitrile → 1-Phenylcyclopropanemethanamine

HRID 74747

Reaktionsgleichung

Reaktionsgleichung von HRID 74747
[C:1]1([C:7]2([C:10]#[N:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]1([C:7]2([CH2:10][NH2:11])[CH2:8][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 702881-PhenylcyclopropanecarbonitrileHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 702871-Phenylcyclopropanemethanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 1-phenylcyclopropanecarbonitrile (50 g, 0.34 mol, 1 eq.) in tetrahydrofuran (500 mL, 0.7 M) at 0° C. was added lithium aluminum hydride (23 g, 0.35 mol, 1.03 eq.). The reaction mixture was stirred at 0° C. for one hour and then at reflux for one hour. The reaction mixture was then cooled down and quenched with water (23 mL) and a 15% aqueous sodium hydroxide solution (69 mL). The mixture was filtered and concentrated in vacuo to afford #*1 (36 g, 72%). LC-MS: m/z 148.1 [M+H+], retention time=0.86 minutes; 1H NMR (400 MHz, CDCl3) δ 7.2-7.4 (m, 5H), 2.78 (s, 2H), 1.19 (br s, 2H), 0.72-0.84 (m, 4H).

Aufarbeitung

  1. temperatureat reflux for one hour
  2. temperatureThe reaction mixture was then cooled down
  3. customquenched with water (23 mL)
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated in vacuo
  6. customto afford #*1 (36 g, 72%)

Quellen und Nachweise

ORD-Eintrag
ord-38f440307c9f4c8baf1bb6fa411de794
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828401B2

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