Aluminium lithium hydride → 4-[2-(3-Methyl-butylamino)-thiazol-4-yl]-benzylamine

HRID 1191071Notes

Reaction equation

HRID 1191071 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][CH:8]([CH3:25])[CH2:9][CH2:10][NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)[N:16]=1>C1COCC1>[CH3:7][CH:8]([CH3:25])[CH2:9][CH2:10][NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17]2[CH:18]=[CH:19][C:20]([CH2:21][NH2:22])=[CH:23][CH:24]=2)[N:16]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 244317014-[2-(3-Methyl-butylamino)-thiazol-4-yl]-benzonitrile

Product 1

HCID 598288274-[2-(3-Methyl-butylamino)-thiazol-4-yl]-benzylamineYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Add lithium aluminum hydride (210 mg, 5.5 mmol) portionwise over 3 min to a solution of 4-[2-(3-methyl-butylamino)-thiazol-4-yl]-benzonitrile (500 mg, 1.8 mmol) in THF (20 mL) at room temperature under a nitrogen atmosphere. Stir the mixture for 1 h at 60° C. Cool the mixture, quench slowly with water (0.2 mL) and 1N NaOH (0.2 mL). Add sodium sulfate to absorb residual water, filter the mixture through Celite®, wash with DCM (50 mL) and concentrate in vacuo. Purify the residue by SCX chromatography to obtain the desired intermediate (493 mg, 97%). MS (ES+) m/z: 276 (M+H)+.

Workup

  1. temperatureCool the mixture
  2. customquench slowly with water (0.2 mL) and 1N NaOH (0.2 mL)
  3. customAdd sodium sulfate to absorb residual water
  4. filtrationfilter the mixture through Celite®
  5. washwash with DCM (50 mL)
  6. concentrationconcentrate in vacuo
  7. customPurify the residue by SCX chromatography

Sources & evidence

ORD record
ord-9f1741e1679c403ca6f0d4a053bfff13
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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