Methyl iodide → HCID 19753882, compound

HRID 1588814Notes

Reaction equation

HRID 1588814 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].CI.[C:25](OCC)(=O)C>CN(C)C=O.O>[CH3:25][N:8]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1)=[O:14])[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 19753952HCID 19753952, compound

Product 1

HCID 19753882HCID 19753882, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[5-(N-t-butoxycarbonylamino)valeryl]morpholine (1.656 g) in dry N,N-dimethylformamide (20 ml) were added sodium hydride (60% dispersion in mineral oil: 347 mg) and methyl iodide (2.462 g) at 0°-5° C. under nitrogen atmosphere. After being stirred for 6 hours at room temperature, the reaction mixture was added to ethyl acetate (200 ml) and water (200 ml). The organic layer was washed with 0.5N hydrochloric acid (200 ml), water (200 ml), aqueous sodium bicarbonate (200 ml), water (200 ml) and brine (200 ml) successively, and dried over magnesium sulfate. Evaporation of the solvent gave 4-[5-(N-methyl-N-t-butoxycarbonylamino)valeryl]morpholine (1.093 g) as an oil.

Workup

  1. washThe organic layer was washed with 0.5N hydrochloric acid (200 ml), water (200 ml), aqueous sodium bicarbonate (200 ml), water (200 ml) and brine (200 ml) successively
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-73840230890445ecaed587af34d11818
Source dataset
uspto-grants-1993_06
Patent number
US05223489

Reaction notes

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