Sodium hydride → HCID 59441807, compound

HRID 1014341Notes

Reaction equation

HRID 1014341 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][OH:22])[CH2:16][CH2:15]1.[H-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][O:22][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=2)[CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2311841-(2-Hydroxyethyl)-4-methylpiperazineHCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 59441807HCID 59441807, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-fluoro-2-(methyloxy)-1-nitrobenzene (1 g, 5.8 mmol) in 20 mL of anhydrous DMF was added 2-(4-methyl-1-piperazinyl)ethanol (1.09 g, 7.6 mmol). Sodium hydride (60%) (467 mg, 11.68 mmol) was added portionwise. The reaction was stirred at rt for 30 min at which time the reaction was diluted with ethyl acetate and washed with water and a saturated sodium chloride solution. Solvents were removed under reduced pressure to give 1.7 g of crude 1-methyl-4-(2-{[3-(methyloxy)-4-nitrophenyl]oxy}ethyl)piperazine as a yellow solid. ESIMS (M+H)+=296.

Workup

  1. washwashed with water
  2. customSolvents were removed under reduced pressure

Sources & evidence

ORD record
ord-930607e495884288adfcbed033e49561
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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