Sodium hydride → HCID 59442047, compound

HRID 1014345Notes

Reaction equation

HRID 1014345 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][CH2:22][OH:23])[CH2:16][CH2:15]1.[H-].[Na+]>CN(C=O)C>[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][O:23][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

5

Reactant 3

HCID 24758Sodium hydrideHCID 792083-(4-Methyl-1-piperazine)propan-1-olHCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 59442047HCID 59442047, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-fluoro-2-(methyloxy)-1-nitrobenzene (1 g, 5.8 mmol) in 20 mL of anhydrous DMF was added 3-(4-methyl-1-piperazinyl)-1-propanol (1.2 g, 7.59 mmol). Sodium hydride (60%) (467 mg, 11.68 mmol) was added portionwise and the reaction was stirred at rt for 90 min at which time it was quenched with a solution of saturated NH4Cl (5 mL) and most of the DMF was removed under reduced pressure. The residue was diluted with ethyl acetate and washed with a minimum amount of water and a saturated sodium chloride solution, dried over Na2SO4 and filtered. Solvents were removed under reduced pressure to give 1-methyl-4-(3-{[3-(methyloxy)-4-nitrophenyl]oxy}propyl)piperazine as a yellow solid (1.8 g total isolated, some residual DMF in product) (ESIMS (M+H)+=311)

Workup

  1. customwas quenched with a solution of saturated NH4Cl (5 mL) and most of the DMF
  2. customwas removed under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with a minimum amount of water
  5. dry with materiala saturated sodium chloride solution, dried over Na2SO4
  6. filtrationfiltered
  7. customSolvents were removed under reduced pressure

Sources & evidence

ORD record
ord-21647caa28d9401e9fe76fe243eaabb8
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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