Aluminium lithium hydride → HCID 178483030, compound

HRID 1620131Notes

Reaction equation

HRID 1620131 reaction equation
C(O[C:6](=O)[NH:7][CH:8]([C:12]1[NH:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:16]=1)[CH:9]([CH3:11])[CH3:10])(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:6][NH:7][CH:8]([C:12]1[NH:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:16]=1)[CH:9]([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178449784HCID 178449784, compound

Product 1

HCID 178483030HCID 178483030, compoundYield 843.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of [2-methyl-1-(4-phenyl-1-H-imidazol-2-yl)-propyl]-carbamic acid tert-butyl ester (0.095 g, 0.30 mmol) in THF (2.0 mL) was added dropwise over 10 min to a refluxing 1.0 M solution of LiAlH4 in THF (3.0 mL). The reaction was maintained at reflux for 2 h, cooled to room temperature, and quenched by sequential treatment with 0.11 mL of cold water (5° C.), 0.11 mL of 15% NaOH in aqueous solution, and 0.33 mL of cold water (5° C.). The resultant solid was removed by suction filtration and the filtrate (pH 8-9) was extracted three times with EtOAc. The combined organic fractions were dried over MgSO4, filtered, and concentrated to afford 0.58 g (84%) of methyl-[2-methyl-1-(4-phenyl-1H-imidazol-2-yl)-propyl]-amine as a light yellow oil (HPLC: 97% @ 254 nm and 214 nm). 1H NMR (300 MHz, CDCl3): δ 7.69 (2H, d, J=7.4 Hz), 7.36 (2H, t, J=7.6 Hz), 7.26 (1H, s), 7.25-7.20 (1H, m), 3.62 (1H, d, J=6.3 Hz), 2.35 (3H, s), 2.06 (1H, m), 0.99 (3H, d, J=6.7 Hz), 0.89 (3H, d, J=6.7 Hz); MS (ES+) (relative intensity): 230.2 (100) (M+1).

Workup

  1. temperatureThe reaction was maintained
  2. temperatureat reflux for 2 h
  3. customquenched by sequential treatment with 0.11 mL of cold water (5° C.), 0.11 mL of 15% NaOH in aqueous solution, and 0.33 mL of cold water (5° C.)
  4. customThe resultant solid was removed by suction filtration
  5. extractionthe filtrate (pH 8-9) was extracted three times with EtOAc
  6. dry with materialThe combined organic fractions were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cad11ea8ec174f15819cad6c82cfa5fe
Source dataset
uspto-grants-2014_07
Patent number
US08772325B2

Reaction notes

Loading…