Cyclopentanone → 1-[Bis(phenylmethyl)amino]cyclopentanecarbonitrile

HRID 20811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 20811
Cl.[CH2:2]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:17]1(=O)[CH2:21][CH2:20][CH2:19][CH2:18]1.[C-:23]#[N:24].[K+]>C(O)C.O>[C:11]1([CH2:10][N:9]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:17]2([C:23]#[N:24])[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

6

Edukt 3

HCID 8452CyclopentanoneHCID 9032Potassium CyanideHCID 13000629Benzenemethanamine, N-(phenylmethyl)-, hydrochloride (1:1)

Produkt 1

HCID 593477851-[Bis(phenylmethyl)amino]cyclopentanecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To an ice-cooled suspension of dibenzylamine hydrochloride (13.5 g; 0.058 mol) and cyclopentanone (4.86 g; 0.058 mol) in 25% ethanol in water (100 ml) was added ethanol (60 ml) and a solution of potassium cyanide (3.78 g; 0.058 mol) in water (35 ml) dropwise over 20 minutes with stirring. After 6 days the reaction mixture was extracted with ethyl acetate, washed with sodium bicarbonate solution, dried (Na2SO4) and evaporated in vacuo to afford the title compound as an off white solid (8.32 g, 49%). 1H NMR (CDCl3) δ: 1.72 (6H, m), 2.12 (2H, m), 3.78 (4H, m), 7.1-7.3 (10H, m); Mass Spectrum (Electrospray LC/MS): Found 264 (MH+−HCN). C20H22N2 requires 290. Ret. time 1.88 min.

Aufarbeitung

  1. extractionAfter 6 days the reaction mixture was extracted with ethyl acetate
  2. washwashed with sodium bicarbonate solution
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e9b1ab97345d4dc9918fcfef0393f96d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745642B2

Notizen zur Reaktion

Wird geladen…