Sodium Hydroxide → 4-[3-Nitro-5-(trifluoromethyl)benzyl]morpholine

HRID 2095103Notes

Reaction equation

HRID 2095103 reaction equation
[N:1]1([C:7]([C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([N+:19]([O-:21])=[O:20])[CH:10]=2)=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[N+:19]([C:11]1[CH:10]=[C:9]([CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=1)[CH2:7][N:1]1[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 219549894-(3-Nitro-5-trifluoromethyl-benzoyl)-morpholine

Product 1

HCID 219550054-[3-Nitro-5-(trifluoromethyl)benzyl]morpholine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of morpholin-4-yl-(3-nitro-5-(trifluoromethyl)phenyl)methanone (304 mg, 1.0 mmol) in 15 mL of THF was added lithium aluminum hydride (152 mg, 4 mmol) in THF (7 mL) under nitrogen. The dark colored solution was refluxed for 2 hours and then cooled. NaOH solution was added (0.5 N, 15 mL) dropwise. The basic solution was washed with methylene chloride (3×40 mL) and the pooled organic layers were washed with HCl solution (5%). The aqueous layer was separated, basified with NaOH to pH 8, and extracted with ethyl acetate. The ethyl acetate solution was dried over anhydrous Na2SO4. The solution was used in further reactions without further work-up.

Workup

  1. temperatureThe dark colored solution was refluxed for 2 hours
  2. temperaturecooled
  3. washThe basic solution was washed with methylene chloride (3×40 mL)
  4. washthe pooled organic layers were washed with HCl solution (5%)
  5. customThe aqueous layer was separated
  6. extractionextracted with ethyl acetate
  7. dry with materialThe ethyl acetate solution was dried over anhydrous Na2SO4

Sources & evidence

ORD record
ord-581b32110bbe442bac18a17c69b79843
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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