Aluminium lithium hydride → 4-cyclopropyl-N-(2-methoxyethyl)aniline

HRID 63658Notes

Reaction equation

HRID 63658 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([NH:10][C:11](=O)[CH2:12][O:13][CH3:14])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.O.CCOC(C)=O>[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][O:13][CH3:14])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 118597819N-(4-cyclopropylphenyl)-2-methoxyacetamide

Product 1

HCID 1185978844-cyclopropyl-N-(2-methoxyethyl)anilineYield 79%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of this N-(4-cyclopropylphenyl)-2-methoxyacetamide in THF (20 mL) was added LAH (5.0 mL, 2.4 M in THF, 12 mmol) at 0° C. The reaction was stirred at r.t. for 2 h. The solution was diluted with water (0.5 mL) and EtOAc (30 mL), dried (Na2SO4), and concentrated. Purification by silica gel chromatography (0% to 15% MeOH/DCM) gave 912 mg (79%) of the title compound as a yellow oil. [M+H] Calc'd for C12H17NO, 192. Found, 192.

Workup

  1. dry with materialdried (Na2SO4)
  2. concentrationconcentrated
  3. customPurification by silica gel chromatography (0% to 15% MeOH/DCM)

Sources & evidence

ORD record
ord-e5e164667de04aa880fd0ce95e3a7ec9
Source dataset
uspto-grants-2016_09
Patent number
US09447046B2

Reaction notes

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