Water → 2-(3,4-Dimethoxyphenoxy)ethan-1-amine

HRID 458793Notes

Reaction equation

HRID 458793 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[O:12][CH2:13][C:14]#[N:15].O.C(Cl)Cl.CO>C1COCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[O:12][CH2:13][CH2:14][NH2:15]

Participants

6

Reactant 4

HCID 962WaterHCID 189913533,4-DimethoxyphenoxyacetonitrileHCID 21226129Dichloromethane methanolHCID 21226445Aluminium lithium hydride

Product 1

HCID 122988912-(3,4-Dimethoxyphenoxy)ethan-1-amineYield 77.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold (0° C.) suspension of LiAlH4 (1.73 g, 45.6 mmol) in anhydrous THF (72 ml), was added dropwise a solution of (3,4-dimethoxy-phenoxy)-acetonitrile (5.88 g, 30.4 mmol) in anhydrous THF (42 ml). The resulting mixture was allowed to warm-up and stirred at RT for 20 h under nitrogen. The reaction mixture was combined with a mixture of H2O/2N NaOH(aq) (4/1) to destroy the excess of LiAlH4. The white suspension was filtered and the solid was washed with CH2Cl2. The combined organic phases were dried over anhydrous MgSO4, filtered and concentrated to give a crude oil. Flash chromatography (CH2Cl2/MeOH: 9/1) gave the title product (4.65 g, 77%).

Workup

  1. temperatureto warm-up
  2. customto destroy the excess of LiAlH4
  3. filtrationThe white suspension was filtered
  4. washthe solid was washed with CH2Cl2
  5. dry with materialThe combined organic phases were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude oil

Sources & evidence

ORD record
ord-0f342057c6454538a3ea492f11d02010
Source dataset
uspto-grants-2007_03
Patent number
US07192950B2

Reaction notes

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