Imidazole → HCID 68976392, Verbindung

HRID 749445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 749445
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][NH:13][CH3:14])[CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.N1C=CN=C1.[CH:20]([Si:23]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])Cl)([CH3:22])[CH3:21]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:9][CH2:10][O:11][Si:23]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:20]([CH3:22])[CH3:21])[CH2:12][NH:13][CH3:14])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 69278839HCID 69278839, Verbindung

Produkt 1

HCID 68976392HCID 68976392, VerbindungAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-(4-Bromophenyl)-4-(methylamino)butan-1-ol (see Chem. Pharm. Bull. 46, 1998, 242; 1.77 g, 6.86 mmol) was dissolved in CH2Cl2 (100 mL) at 0° C. under argon. Imidazole (1.22 g, 17.9 mmol) was added, the mixture stirred for 10 min and then triisopropylchlorosilan (3.16 g, 16.4 mmol) was added with cooling. The mixture was stirred at room temperature for 48 h and then washed twice with water (100 mL) and brine. The solvent was removed by evaporation and the residue flash chromatographed on silica gel (CH2Cl2-Methanol-NH4OH, 15:1:0.1). There was obtained 2.17 g (75%) of {2-(4-bromophenyl)-4-[(triisopropylsilyl)oxy]butyl}methylamine as an oil. 1H NMR (300 MHz, CDCl3): 0.9-1.1 (m, 21H), 1.6-1.9 (m, 2H), 2.4 (s, 3H), 2.7-2.8 (m, 2H), 3.0-3.1 (m, 1H), 3.4-3.6 (m, 2H), 7.1 (d, 2H), 7.4 (d, 2H).

Aufarbeitung

  1. temperaturewith cooling
  2. stirringThe mixture was stirred at room temperature for 48 h
  3. washwashed twice with water (100 mL) and brine
  4. customThe solvent was removed by evaporation
  5. customthe residue flash chromatographed on silica gel (CH2Cl2-Methanol-NH4OH, 15:1:0.1)

Quellen und Nachweise

ORD-Eintrag
ord-e4c72d359eaa4bfa9ae3bc40df150b3f
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402581B2

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