Aluminium lithium hydride → 6-Aminomethyl-2-cyclohexylmethyl-benzothiazole

HRID 911574Notes

Reaction equation

HRID 911574 reaction equation
[CH:1]1([CH2:7][C:8]2[S:9][C:10]3[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:18][CH2:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([CH2:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[S:9][C:10]=2[CH:16]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 667067722-Cyclohexylmethyl-benzothiazole-6-carbonitrile

Product 1

HCID 576562366-Aminomethyl-2-cyclohexylmethyl-benzothiazoleYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 2-cyclohexylmethyl-benzothiazole-6-carbonitrile (0.2 g, 0.55 mmol) in anhydrous THF (2 mL) and add slowly 1M lithium aluminum hydride in THF (0.82 mL, 0.82 mmol) at room temperature. Stir the reaction mixture at room temperature for 0.5 h. Quench the reaction mixture with water until a granular precipitate starts to form and filter through a pad of Celite®. Evaporate the solvent and purify the residue by SCX chromatography to obtain the title compound as a yellow oil (0.1 g, 92%). MS (ES+) m/z: 260 (M+H)+.

Workup

  1. customQuench the reaction mixture with water until a granular precipitate
  2. customto form
  3. filtrationfilter through a pad of Celite®
  4. customEvaporate the solvent
  5. custompurify the residue by SCX chromatography

Sources & evidence

ORD record
ord-15c4df681fde4bee9321708f90119272
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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