2-Methoxyethylamine → HCID 59540249, compound

HRID 923390Notes

Reaction equation

HRID 923390 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].C(=O)([O-])[O-].[K+].[K+].[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1)([O-:14])=[O:13]>CN(C=O)C>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:19][C:18]1[CH:21]=[CH:22][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=1)[CH2:19][C:18]1[CH:21]=[CH:22][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromide

Product 1

HCID 59540249HCID 59540249, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methoxyethylamine (0.343 mL, 3.99 mmol) in DMF (20.0 mL) at room temperature was added potassium carbonate (0.964 mL, 15.98 mmol) followed by 4-nitrobenzyl bromide (1.812 g, 8.39 mmol). The reaction was stirred for 2 hours then quenched with water, extracted with EtOAc and concentrated. The residue was purified by chromatography (20% to 40% EtOAc-hexane) to provide the title compound. MS (DCI) m/z 346 (M+H)+.

Workup

  1. customthen quenched with water
  2. extractionextracted with EtOAc
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography (20% to 40% EtOAc-hexane)

Sources & evidence

ORD record
ord-e8a100fd560141139ef82b715d269828
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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