4-(3-Nitro-5-trifluoromethyl-benzoyl)-morpholine → 4-[3-Nitro-5-(trifluoromethyl)benzyl]morpholine
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>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
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of morpholin-4-yl-(3-nitro-5-(trifluoromethyl)phenyl)methanone (457 mg, 1.5 mmol) in THF (5 mL) was added dropwise a solution of borane tetrahydrofuran complex solution (3.1 mL, 3.1 mmol) at ambient temperature and the mixture was heated under reflux for 30 minutes, then cooled. The solvent was evaporated. Aqueous HCl (5 mL) was added and the resulting mixture was heated at 100° C. for 1 hour, then cooled and extracted with ether. The acidic aqueous layer was separated, basified to pH 8 with NaOH and extracted with ether. The ether solution was dried over anhydrous Na2SO4. Evaporation of ether provided 168 mg (0.57 mmol) of 4-(3-Nitro-5-trifluoromethylbenzyl)morpholine (38%).
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 30 minutes
- temperaturecooled
- customThe solvent was evaporated
- additionAqueous HCl (5 mL) was added
- temperaturecooled
- extractionextracted with ether
- customThe acidic aqueous layer was separated
- extractionextracted with ether
- dry with materialThe ether solution was dried over anhydrous Na2SO4
- customEvaporation of ether
Sources & evidence
- ORD record
- ord-7d6c196dc4464aa3b0a5ceb2b1eb2e4f
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07875728B2
Reaction notes
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