Aluminum(III) Chloride → HCID 58174254, compound

HRID 1255892Notes

Reaction equation

HRID 1255892 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:11][C:12]([F:30])([F:29])[C:13]1[CH:28]=[CH:27][C:16]([O:17][C:18]2[N:23]=[CH:22][C:21]([CH2:24][C:25]#[N:26])=[CH:20][CH:19]=2)=[CH:15][CH:14]=1>CCOCC.C1COCC1>[F:29][C:12]([F:11])([F:30])[C:13]1[CH:28]=[CH:27][C:16]([O:17][C:18]2[N:23]=[CH:22][C:21]([CH2:24][CH2:25][NH2:26])=[CH:20][CH:19]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 58174138HCID 58174138, compound

Product 1

HCID 58174254HCID 58174254, compoundYield 39.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of AlCl3 (268 mg, 1.8 mmol) in Et2O cooled to 0° C. in an ice bath was added LiAlH4 (66 mg, 1.8 mmol) in one portion, under N2. After stirring 15 min, a solution of [6-(4-trifluoromethylphenoxy)-pyridin-3-yl]-acetonitrile (500 mg, 1.8 mmol) in Et2O (2 mL) and THF (1 mL) was added dropwise resulting in an exotherm. The reaction was allowed to cool to room temperature, and after 2 h, the reaction was quenched by careful addition of 5 mL of saturated aqueous ammonium chloride. The resulting mixture was made alkaline by addition of 2M NaOH solution. The precipitate which formed was removed by filtration through Celite. The filtrate phases were separated, and the aqueous phase was extracted 3 times with Et2O. The pooled organic fractions were dried with Na2SO4 and suction filtered. The solvent was removed in vacuo to yield 2-[6-(4-trifluoromethylphenoxy)-pyridin-3-yl]-ethylamine (200 mg), as a brown oil.

Workup

  1. customresulting in an exotherm
  2. waitafter 2 h
  3. customthe reaction was quenched by careful addition of 5 mL of saturated aqueous ammonium chloride
  4. additionby addition of 2M NaOH solution
  5. customThe precipitate which formed
  6. customwas removed by filtration through Celite
  7. customThe filtrate phases were separated
  8. extractionthe aqueous phase was extracted 3 times with Et2O
  9. dry with materialThe pooled organic fractions were dried with Na2SO4 and suction
  10. filtrationfiltered
  11. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-241c38ed318b4564aec0244a8649077b
Source dataset
uspto-grants-2013_06
Patent number
US08461164B2

Reaction notes

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