Aluminium lithium hydride → [4-Aminomethyl-1-(3-fluorophenyl)-4-methyl-cyclohexyl]-dimethylamine

HRID 76938Notes

Reaction equation

HRID 76938 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH3:26])[C:9]1([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)[CH2:14][CH2:13][C:12]([CH3:18])([CH:15]=[N:16]O)[CH2:11][CH2:10]1>C1COCC1>[NH2:16][CH2:15][C:12]1([CH3:18])[CH2:11][CH2:10][C:9]([N:8]([CH3:26])[CH3:7])([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 87523172HCID 87523172, compound

Product 1

HCID 68632146[4-Aminomethyl-1-(3-fluorophenyl)-4-methyl-cyclohexyl]-dimethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminium hydride (440 mg, 11.6 mmol) was suspended in abs. THF (50 mL) in argon, mixed in drops with a solution of the title compound of step 3 (1.54 g, 5.53 mmol) in abs. THF (20 mL) and boiled for 4 h with reflux. The batch was then hydrolysed with water (10 mL) at 10° C. and filtered off over diatomaceous earth. The THF was removed in a vacuum, the residue adjusted to pH 11 with 1N NaOH and extracted with ethyl acetate. The combined organic phases were dried over Na2SO4, concentrated to low volume in a vacuum and the remaining residue was purified by flash chromatography with MeOH+2% NH3.

Workup

  1. temperaturewith reflux
  2. filtrationhydrolysed with water (10 mL) at 10° C. and filtered off over diatomaceous earth
  3. customThe THF was removed in a vacuum
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. concentrationconcentrated to low volume in a vacuum
  7. customthe remaining residue was purified by flash chromatography with MeOH+2% NH3

Sources & evidence

ORD record
ord-edf67767051846449cf81616ab7a919b
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

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