Isoamylamine → HCID 18676169, Verbindung

HRID 1635576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1635576
[CH2:1]([NH2:6])[CH2:2][CH:3]([CH3:5])[CH3:4].ClC1C=CC=CC=1C[N:11]1[C:15]([CH3:16])=[C:14]([CH3:17])[N:13]=[C:12]1[CH2:18]Cl.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:16][C:15]1[N:11]=[C:12]([CH2:18][NH:6][CH2:1][CH2:2][CH:3]([CH3:5])[CH3:4])[NH:13][C:14]=1[CH3:17]

Komponenten

5

Edukt 3

HCID 7894IsoamylamineHCID 11430Potassium CarbonateHCID 12011185HCID 12011185, Verbindung

Produkt 1

HCID 18676169HCID 18676169, VerbindungAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a solution of 7 ml (60 mmol) of isoamylamine in 3 ml of acetonitrile is added slowly a solution of 1-(2′-chlorobenzyl)-4,5-dimethyl-2-chloromethylimidazole in 10 ml of acetonitrile followed by added 1.5 g (10.8 mmol) of potassium carbonate powder. The reaction mixture is stirred overnight at room temperature under nitrogen and excess isoamylamine is evaporated in vacuo. The residue is dissolved in 50 ml of ethyl acetate and 25 ml of water. The ethyl acetate layer is separated, washed with brine, dried over anhydrous sodium sulfate and evaporated in vacuo. The crude product is purified by preparative TLC [silica gel, chloroform-methanol-ammonium hydroxide (90:10:1)] to give 1.39 g (46%) of N-[(4,5-dimethylimidazol-2-yl)methyl]-(3-methylbutyl)amine as a yellow oil. MS m/z (M++1) 320; 1H-NMR 400 MHz(δ, CDCl3): 0.81 (6H, d, J=6.4 Hz), 1.25 (2H, m), 1.51 (1H, m), 1.96 (3H, s), 2.17 (3H, s), 2.56 (2H, m), 3.68 (2H, s), 5.21 (2H, s), 6.39 (1H, d, J=7.6 Hz), 7.13 (1H, m), 7.19 (1H, m), 7.37 (1H, m) ppm.

Aufarbeitung

  1. customexcess isoamylamine is evaporated in vacuo
  2. dissolutionThe residue is dissolved in 50 ml of ethyl acetate
  3. customThe ethyl acetate layer is separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. customThe crude product is purified by preparative TLC [silica gel, chloroform-methanol-ammonium hydroxide (90:10:1)]

Quellen und Nachweise

ORD-Eintrag
ord-b2fdecc3cf4e4be0ba07bd509a676881
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06509366B2

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