Water → C-(5-(4-fluorophenoxy)thiophen-2-yl)methylamine

HRID 2080071Notes

Reaction equation

HRID 2080071 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[S:11][C:10]([C:12]#[N:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.FC1C=CC(O)=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1.CO.C(OCC)(=O)C>[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[S:11][C:10]([CH2:12][NH2:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 97324-FluorophenolHCID 21226445Aluminium lithium hydrideHCID 231305625-(4-Fluorophenoxy)thiophene-2-carbonitrile

Product 1

HCID 23130478C-(5-(4-fluorophenoxy)thiophen-2-yl)methylamine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 5-(4-fluorophenoxy)thiophene-2-carbonitrile described in Preparation Example 27 (containing 4-fluorophenol) (3.7 g) in tetrahydrofuran (40 mL) was added lithium aluminum hydride (1.3 g, 34 mmol), and the solution was stirred at room temperature for 30 minutes. Water and ethyl acetate were added to the reaction solution, which was then partitioned, the solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (ethyl acetate, then ethyl acetate:methanol=4:1), and the title compound (1.2 g, 5.4 mmol) was obtained as a brown oil.

Workup

  1. customwas then partitioned
  2. customthe solvent was evaporated in vacuo
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-28b7ae8e9c4c47d3adcabf74637bcf5f
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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