Water → (4-Aminomethyl-2-trifluoromethyl-phenyl)-dimethyl-amine

HRID 1385168Notes

Reaction equation

HRID 1385168 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[C:11]([F:14])([F:13])[F:12].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH2:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([N:2]([CH3:1])[CH3:15])=[C:4]([C:11]([F:12])([F:13])[F:14])[CH:5]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 217328174-(Dimethylamino)-3-(trifluoromethyl)benzonitrile

Product 1

HCID 18543285(4-Aminomethyl-2-trifluoromethyl-phenyl)-dimethyl-amineYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-dimethylamino-3-trifluoromethylbenzonitrile (0.35 g) in tetrahydrofuran (2 mL) is slowly added to a suspension of lithium aluminum hydride (0.1 g) in tetrahydrofuran (2 mL) at 0° C. and stirred under an atmosphere of argon for 2 hours. While at 0° C. water (0.1 mL) is slowly added followed by 5% sodium hydroxide (0.1 mL) and water (0.3 mL). The resulting gray solid is filtered and washed with tetrahydrofuran. The filtrates are collected and concentrated under reduced pressure and the resulting oil is chromatographed over silica gel (15% methanol in methylene chloride is used as the eluant) to provide the desired product as a pale orange oil (0.164 g).

Workup

  1. filtrationThe resulting gray solid is filtered
  2. washwashed with tetrahydrofuran
  3. customThe filtrates are collected
  4. concentrationconcentrated under reduced pressure
  5. customthe resulting oil is chromatographed over silica gel (15% methanol in methylene chloride

Sources & evidence

ORD record
ord-94fa1e7a221940c99a6f233b3a32201e
Source dataset
uspto-grants-2001_07
Patent number
US06262082B1

Reaction notes

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