Sodium Hydroxide → 3,3-Dimethylbutyl-2-thiophenemethanamine

HRID 359983Notes

Reaction equation

HRID 359983 reaction equation
COCCO[AlH2-]OCCOC.[Na+].[CH3:13][C:14]([CH3:26])([CH3:25])[CH2:15][CH2:16][C:17]1[CH:21]=[CH:20][S:19][C:18]=1[C:22]([NH2:24])=O.[OH-].[Na+]>C1(C)C=CC=CC=1.O1CCCC1>[CH3:13][C:14]([CH3:26])([CH3:25])[CH2:15][CH2:16][C:17]1[CH:21]=[CH:20][S:19][C:18]=1[CH2:22][NH2:24]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 16684438Red-AlHCID 200645453,3-Dimethylbutyl-2-thiophene carboxamide

Product 1

HCID 200646443,3-Dimethylbutyl-2-thiophenemethanamineYield 85.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 17.0 ml of Vitride® T [sodium dihydrobis(2-methoxyethoxy)aluminate (70% solution in toluene)] in 50 ml of toluene, was added dropwise a solution of 5.0 g of 3,3-dimethylbutyl-2-thiophene carboxamide in 50 ml of dried tetrahydrofuran. The resulting mixture was heated at reflux for 2 hours, then cooled. The complex was decomposed by adding dropwise 30 ml of 2.5N sodium hydroxide. The mixture was stirred for one hour. The layers were separated and the organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated in vacuo and gave a light brown liquid. Kugelrohr distillation (75° C./0.15 mm of mercury) gave 4.0 g (82% yield) of the desired product.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperaturecooled
  4. customThe layers were separated
  5. washthe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated in vacuo
  9. customgave a light brown liquid
  10. distillationKugelrohr distillation (75° C./0.15 mm of mercury)

Sources & evidence

ORD record
ord-2f3ec75061b94b0f8d2052b136a1fa97
Source dataset
uspto-grants-1991_03
Patent number
US05003106

Reaction notes

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