Trifluoroacetic acid → 2-Butylaminomethylbenzimidazole

HRID 1601081Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1601081
C([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17]Br)(OC(C)(C)C)=O.[CH2:19]([NH2:23])[CH2:20][CH2:21][CH3:22].C(O)(C(F)(F)F)=O>C1COCC1.C(Cl)Cl>[CH2:19]([NH:23][CH2:17][C:9]1[NH:8][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=1)[CH2:20][CH2:21][CH3:22]

Komponenten

6

Edukt 3

HCID 6422Trifluoroacetic acidHCID 8007ButylamineHCID 11381356tert-butyl 2-(bromomethyl)-1H-benzo[d]imidazole-1-carboxylate

Produkt 1

HCID 131694082-ButylaminomethylbenzimidazoleAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-BOC-2-bromomethylbenzimidazole (2.00 g, 6.4 rnmol) in dry THF (20 mL) was added n-butylamine (1.2 g, 15.4 mmol). After stirring at RT overnight, the mixture was concentrated. The residue was taken up in H2O and extracted with CH2Cl2. The organic extracts were dried over MgSO4 and concentrated to give a brown residue, which was dissolved in CH2Cl2 (15 mL) and treated with TFA (5 mL). The resulting mixture was stirred at RT overnight then was concentrated. The residue was taken up in H2O, and the solution was neutralized with 2.5 N NaOH. CH2Cl2 extraction, drying (MgSO4), concentration, and silica gel chromatography (2% MeOH/CH2Cl2) gave the title compound as a yellow oil (0.91 g, 70%): 1H NMR (250 MHz, CDCl3) δ 0.79 (t, J=7.2 Hz, 3H), 1.23 (m, 2H), 1.54 (m, 2H), 3.35 (t, J=7.2 Hz, 2H), 4.55 (s, 2H), 7.25 (m, 2H), 7.48 (m, 1H), 7.75 (m, 1H).

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic extracts were dried over MgSO4
  4. concentrationconcentrated
  5. customto give a brown residue, which
  6. stirringThe resulting mixture was stirred at RT overnight
  7. concentrationthen was concentrated
  8. extractionCH2Cl2 extraction
  9. customdrying
  10. concentration(MgSO4), concentration, and silica gel chromatography (2% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-e2a66163d174462cb050b5800bd9c732
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05977101

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