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

HRID 2041441Notes

Reaction equation

HRID 2041441 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-a0bfa5986a0a4011836eb31926ab37db
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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