Aluminium lithium hydride → N-(8-methoxytetralin-2-yl)-N-propyl-N-[2-(2-thienyl)ethyl]amine

HRID 2042769Notes

Reaction equation

HRID 2042769 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([N:13]([CH2:22][CH2:23][CH3:24])[C:14](=O)[CH2:15][C:16]1[S:17][CH:18]=[CH:19][CH:20]=1)[CH2:9][CH2:8]2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([N:13]([CH2:22][CH2:23][CH3:24])[CH2:14][CH2:15][C:16]1[S:17][CH:18]=[CH:19][CH:20]=1)[CH2:9][CH2:8]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67251740N-(8-methoxytetralin-2-yl)-N-propyl-2-(2-thienyl)acetamide

Product 1

HCID 53252574N-(8-methoxytetralin-2-yl)-N-propyl-N-[2-(2-thienyl)ethyl]amine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 16 mg (0.05 mmol) of N-(8-methoxytetralin-2-yl)-N-propyl-2-(2-thienyl)acetamide (A4-1: R═OMe, Cy=2-thienyl) in 10 mL dry diethyl ether 0.15 mL of a 1 M solution of LiAlH4 (0.15 mmol) in dry diethyl ether were added dropwise and stirred for 20 hrs at room temperature. The reaction was terminated by adding a saturated aqueous solution of sodium hydrogen carbonate, the solution was filtered through a matrix consisting of Celite™ —MgSO4—Celite™ and subsequently washed with methylenchloride and ethyl acetate. After evaporating the organic solvents in vacuo the residue was purified by flash chromatography on silica gel with a mixture of hexane/ethyl acetate 10/1 in the presence of 0.5% (v/v) dimethylethylamine to get compound (N-(8-methoxytetralin-2-yl)-N-propyl-N-[2-(2-thienyl)ethyl]amine (A5-1: R═OMe, Cy=2-thienyl)).

Workup

  1. customThe reaction was terminated
  2. additionby adding a saturated aqueous solution of sodium hydrogen carbonate
  3. filtrationthe solution was filtered through a matrix
  4. washsubsequently washed with methylenchloride and ethyl acetate
  5. customAfter evaporating the organic solvents in vacuo the residue
  6. customwas purified by flash chromatography on silica gel with a mixture of hexane/ethyl acetate 10/1 in the presence of 0.5% (v/v) dimethylethylamine

Sources & evidence

ORD record
ord-b2ef6f917fe149939a9fbb74bfef77fb
Source dataset
uspto-grants-2013_11
Patent number
US08586603B2

Reaction notes

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