3-Benzyloxyphenylacetonitrile → 2-(3-(Benzyloxy)phenyl)ethanamine

HRID 2114719Notes

Reaction equation

HRID 2114719 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]#[N:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:2]1([CH2:1][O:8][C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][NH2:17])[CH:12]=[CH:13][CH:14]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5198313-BenzyloxyphenylacetonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 2074152-(3-(Benzyloxy)phenyl)ethanamineYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-benzyloxyphenylacetonitrile (11.50 g, 51.50 mmol) in 100 mL of THF at 0° C. was treated with LiAlH4 (3.90 g, 103 mmol) in several portions over 20 minutes. The reaction mixture was warmed to room temperature and stirred for 30 minutes then it was heated at reflux for 6 h. The suspension was cooled to room temperature and quenched by the slow addition of Na2SO4 .10H2O (25 g). The resulting mixture was diluted with 200 mL of CH2Cl2. The organic layer was separated and the remaining salt was rinsed with additional CH2Cl2 (2×50 mL). The combined organic layers were dried over MgSO4, concentrated, and purified by column chromatography (SiO2, hexanes/ethyl acetate, 2:1) to provide the title compound (5.85 g, 51% yield): ES-MS (m/z) 228 [M+H]+.

Workup

  1. temperatureit was heated
  2. temperatureat reflux for 6 h
  3. temperatureThe suspension was cooled to room temperature
  4. customquenched by the slow addition of Na2SO4
  5. additionThe resulting mixture was diluted with 200 mL of CH2Cl2
  6. customThe organic layer was separated
  7. washthe remaining salt was rinsed with additional CH2Cl2 (2×50 mL)
  8. dry with materialThe combined organic layers were dried over MgSO4
  9. concentrationconcentrated
  10. custompurified by column chromatography (SiO2, hexanes/ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-e93b64b232b042f7a1f93e4b42ecde04
Source dataset
uspto-grants-2008_10
Patent number
US07435729B2

Reaction notes

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