Ethanol → 342435-23-8

HRID 1795158Notes

Reaction equation

HRID 1795158 reaction equation
COC1C=C(N)C=C[C:8]=1[O:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16]O[CH2:14][CH2:13]1.[CH2:19]([OH:21])[CH3:20]>[Pd]>[CH3:8][O:9][CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH:20]([CH:19]=[O:21])[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 702EthanolHCID 22185405HCID 22185405, compound

Product 1

HCID 17893954342435-23-8

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4-[2-(2-Methoxy-4-nitro-phenoxy)-ethyl]-morpholine To a solution of (1-(2-hydroxyethyl)-morpholine) (1.94 ml, 16 mmol) in dimethylformamide was added sodium hydride [60% dispersion in oil] (544 mg, 16 mmol). After stirring at room temperature for 10 min, a solution of (1-chloro-2-methoxy-4-nitro-benzene) (3 g, 16 mmol) in dimethylformamide (10 ml) was added dropwise. The reaction mixture was left stirring at room temperature for 16 hours, concentrated, then the residue dissolved in ethyl acetate and washed with water. The organic phase was dried with magnesium sulphate, concentrated and the residue purified by column chromatography on silica gel to afford the title compound; MS(ES+) m/e 283 [M+H]+. Step 2. 3-Methoxy-4-(2-morpholin-4-yl-ethoxy)-phenylamine To a solution of the product of Step 1 (2.3 g, 8.6 mmol) in ethanol (100 ml) was added 10% palladium on charcoal (50 mg). The mixture was then stirred at room temperature under an atmosphere of hydrogen for 16 hours, filtered through celite and concentrated to give the title compound; MS(ES+) m/e 252 [M+H]+.

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c1f4e202548643b8a6af7552c715765a
Source dataset
uspto-grants-2006_04
Patent number
US07026336B1

Reaction notes

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