Methanol → 4-(2-THIENYL)BENZYLAMINE

HRID 1006588Notes

Reaction equation

HRID 1006588 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO>O1CCCC1.ClCCl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 35641934-(2-thienyl)benzonitrileHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 27763324-(2-THIENYL)BENZYLAMINE

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The 4-(2-thienyl)benzonitrile (0.086 g, 0.464 mmol) was dissolved in dry tetrahydrofuran (1.6 ml) before lithium aluminum hydride (0.46 ml, 0.464 mmol, 1 M in THF) was added dropwise. The reaction was allowed to stir at room temperature overnight. TLC (5% methanol in dichloromethane) still showed starting material remaining. Another 1 eq of LAH was added. After an additional hour, the reaction was quenched by the Fieser and Fieser method using wager (17.46 μl), aqueous sodium hydroxide solution (17.46 μl, 15% soln.), and water (52.37 μl) added sequentially to the reaction. The reaction was then diluted with diethyl ether and water and extracted twice with diethyl ether before drying over sodium sulfate and concentrating in vacuo. The residue was carried on crude without any further purification.

Workup

  1. additionwas added dropwise
  2. waitAfter an additional hour
  3. customthe reaction was quenched by the Fieser and Fieser method
  4. additionadded sequentially to the reaction
  5. additionThe reaction was then diluted with diethyl ether and water
  6. extractionextracted twice with diethyl ether
  7. dry with materialbefore drying over sodium sulfate
  8. concentrationconcentrating in vacuo
  9. customThe residue was carried on crude without any further purification

Sources & evidence

ORD record
ord-9b7250e7a5e44ab2927c47a6b5a8765a
Source dataset
uspto-grants-2004_09
Patent number
US06790958B2

Reaction notes

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