Water → C-(5-(3-fluorophenoxy)thiophen-2-yl)methylamine

HRID 2080066Notes

Reaction equation

HRID 2080066 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[S:10][C:9]([C:11]#[N:12])=[CH:8][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(OCC)(=O)C>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[S:10][C:9]([CH2:11][NH2:12])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 231306135-(3-Fluorophenoxy)thiophene-2-carbonitrile

Product 1

HCID 23130606C-(5-(3-fluorophenoxy)thiophen-2-yl)methylamineYield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(3-fluorophenoxy)thiophene-2-carbonitrile described in Preparation Example 22 (670 mg, 3 mmol) in tetrahydrofuran (30 mL) was added lithium aluminum hydride (460 mg, 12 mmol), and the solution was stirred at room temperature for 16 hours. Water and ethyl acetate were added to the reaction solution, which was then partitioned, the organic layer was filtered with NH silica gel, the filtrate was evaporated in vacuo, and the title compound (570 mg, 2.42 mmol, 80.7%) was obtained as a brown oil.

Workup

  1. customwas then partitioned
  2. filtrationthe organic layer was filtered with NH silica gel
  3. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-efebfa5e8509454b8eb7421c76feefbe
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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