Ether hydrochloride → 2-tert-Butyl-1-(cyclohexylmethyl)-N-methyl-1H-benzimidazol-5-amine

HRID 472935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472935
[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([NH:21][C:22](=O)OC)=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.CCOCC.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([NH:21][CH3:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 10953452Ether hydrochlorideHCID 11588208Methyl [2-tert-butyl-1-(cyclohexylmethyl)-1H-benzimidazol-5-yl]carbamateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 116307962-tert-Butyl-1-(cyclohexylmethyl)-N-methyl-1H-benzimidazol-5-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Methyl [2-tert-butyl-1-(cyclohexylmethyl)-1H-benzimidazol-5-yl]carbamate (650 mg, 1.89 mmol) was dissolved in 20 mL of THF at 0° C. under nitrogen. 1M HCl/ether (2.65 mL, 2.65 mmol) was added dropwise and the solution was stirred at 0° C. for 15 min. LiAlH4 (360 mg, 9.45 mmol) was then slowly added and the solution was stirred at rt overnight. The reaction mixture was quenched at 0° C. by addition of MeOH (5 mL) followed by water (10 mL). The solution was diluted with EtOAc and washed with saturated NaHCO3 solution, brine and dried over anhydrous MgSO4. The solvent was evaporated and the product was used directly for Step A without further purification. Yield: 544 mg (96%). 1H NMR (400 MHz, CHLOROFORM-D) δ 1.08 (s, 2H), 1.17 (m, 3H), 1.54 (s, 9H), 1.64 (m, 2H), 1.67 (m, 2H), 1.72 (m, 2H), 2.02 (m, 1H), 2.87 (s, 3H), 4.06 (d, J=7.62 Hz, 2H), 6.60 (dd, J=8.69, 2.25 Hz, 1H), 7.00 (d, J=1.76 Hz, 1H), 7.12 (d, J=8.59 Hz, 1H).

Aufarbeitung

  1. stirringthe solution was stirred at rt overnight
  2. customThe reaction mixture was quenched at 0° C. by addition of MeOH (5 mL)
  3. additionThe solution was diluted with EtOAc
  4. washwashed with saturated NaHCO3 solution, brine
  5. dry with materialdried over anhydrous MgSO4
  6. customThe solvent was evaporated
  7. customthe product was used directly for Step A without further purification

Quellen und Nachweise

ORD-Eintrag
ord-80d2963645324f42aa4f45bc051d9a04
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633235B2

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