Water → C-(5-Phenoxy thiophen-2-yl)methylamine

HRID 2080069Notes

Reaction equation

HRID 2080069 reaction equation
[O:1]([C:8]1[S:12][C:11]([C:13]#[N:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(OCC)(=O)C>O1CCCC1>[O:1]([C:8]1[S:12][C:11]([CH2:13][NH2:14])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 23130496HCID 23130496, compound

Product 1

HCID 23130515C-(5-Phenoxy thiophen-2-yl)methylamineYield 89.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-phenoxythiophene-2-carbonitrile described in Preparation Example 25 (1.4 g, 7.0 mmol) in tetrahydrofuran (30 mL) was added lithium aluminum hydride (1.1 g, 28 mmol), and the solution was stirred at room temperature for 25 minutes. Water and ethyl acetate were added to the reaction solution, this mixed solution was filtered through Celite pad, furthermore, the organic layer was partitioned. The solvent was evaporated in vacuo, and the title compound (1.29 g, 6.3 mmol, 89.9%) was obtained as a brown oil.

Workup

  1. filtrationthis mixed solution was filtered through Celite pad
  2. customfurthermore, the organic layer was partitioned
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-0a262b45c0b847e8bef1c3439f25d82b
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…