Sodium → AP-24592

HRID 1527854Notes

Reaction equation

HRID 1527854 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=2[C:18]([F:21])([F:20])[F:19])[CH2:4][CH2:3]1.[Na]>CC(C)=O.O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=2[C:18]([F:21])([F:19])[F:20])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 5360545SodiumHCID 468389061-Methyl-4-(4-nitro-2-(trifluoromethyl)benzyl)piperazine

Product 1

HCID 46838908AP-24592Yield 64.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A suspension of 1-methyl-4-(4-nitro-2-(trifluoromethyl)benzyl)piperazine (1.23 g, 4 mmol) and sodium hydrosuffite (7.0 g, 85% pure from Aldrich, 40 mmol) in acetone and water (1:1, 20 mL) was refluxed for 3 h. Upon cooling, the volatile components (mainly acetone) were removed on rotavap, and the resulting mixture was subjected to filtration. The solid was thoroughly washed with EtOAc. The combined filtrate was extracted with n-BuOH (4×), and the combined organic layer was washed with saturated aq. NaHCO3, dried (Na2SO4), filtered, concentrated, and the resulting residue was purified by silica gel chromatography (eluted with 5% MeOH/DCM, MeOH was pre-saturated with ammonia gas) to provide 0.71 g of product as a pale yellow solid.

Workup

  1. temperaturewas refluxed for 3 h
  2. temperatureUpon cooling
  3. customthe volatile components (mainly acetone) were removed on rotavap
  4. filtrationthe resulting mixture was subjected to filtration
  5. washThe solid was thoroughly washed with EtOAc
  6. extractionThe combined filtrate was extracted with n-BuOH (4×)
  7. washthe combined organic layer was washed with saturated aq. NaHCO3
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customthe resulting residue was purified by silica gel chromatography (eluted with 5% MeOH/DCM, MeOH was pre-saturated with ammonia gas)

Sources & evidence

ORD record
ord-a1881af8f10044338507ea4a2174e434
Source dataset
uspto-grants-2015_07
Patent number
US09090561B2

Reaction notes

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