Aluminium lithium hydride → HCID 178463772, compound

HRID 1913556Notes

Reaction equation

HRID 1913556 reaction equation
[CH3:1][CH:2]([CH3:19])[CH:3]([NH:15][C:16](=O)[CH3:17])[C:4]1[NH:5][CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:16]([NH:15][CH:3]([C:4]1[NH:5][CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:8]=1)[CH:2]([CH3:19])[CH3:1])[CH3:17]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178474653HCID 178474653, compound

Product 1

HCID 178463772HCID 178463772, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-[2-methyl-1-(4-phenyl-1H-imidazol-2-yl)-propyl]-acetamide (0.077 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 11 h, cooled to rt, 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 0.069 g of a 5:1 mixture (determined by 1H NMR) of ethyl-[2-methyl-1-(4-phenyl-1H-imidazol-2-yl)-propyl]-amine and recovered Cpd 2c as a colorless oil (HPLC: peaks overlap). 1H NMR (300 MHz, CDCl3): δ 7.67 (2H, br s), 7.35 (2H, t, J=7.6 Hz), 7.26-7.17 (2H, m), 3.72 (1H, d, J=6.0 Hz), 2.56 (2H, dq, J=13.0, 7.1 Hz), 2.05 (1H, m), 1.08 (3H, t, J=7.1 Hz), 0.97 (3H, d, J=6.7 Hz), 0.89 (3H, d, J=6.7 Hz); MS (ES+) (relative intensity): 244.2 (100) (M+1). This sample was of sufficient quality to use in the next reaction without further purification.

Workup

  1. temperatureThe reaction was maintained
  2. temperatureat reflux for 11 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-ceab93ede2cd4331b045d948a7eb80f0
Source dataset
uspto-grants-2013_12
Patent number
US08609709B2

Reaction notes

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