p-Fluoronitrobenzene → HCID 68819606, compound
Reaction equation
[H-].[Na+].F[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[CH3:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][OH:22])[CH2:16][CH2:15]1>CN(C=O)C>[CH3:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][O:22][C:4]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=2)[CH2:16][CH2:15]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
200 mg (4.2 mmol) of sodium hydride (55%) is added at 0° C. to a solution of 0.54 g (3.83 mmol) of 1-fluoro-4-nitrobenzene and 0.6 g (4.2 mmol) of 2-(4-methylpiperidin-1-yl)ethanol in 10 mL of DMF under an argon atmosphere. The reaction mixture is stirred for 2 hours at 0° C. and then stirred for a further 1.5 hours at ambient temperature. The reaction mixture is evaporated down and the residue is extracted between water and ethyl acetate. The organic phase is dried, the desiccant is filtered off and the filtrate is evaporated down. The purification is carried out by column chromatography on silica gel (eluant: dichloromethane/methanol (9:1)). Yield: 700 mg (69% of theory); C14H20N2O3 (M=264.32); calc.: molecular ion peak (M+H)+: 265; found: molecular ion peak (M+H)+: 265; Rf value: 0.7 (silica gel, dichloromethane/methanol (9:1)).
Workup
- stirringstirred for a further 1.5 hours at ambient temperature
- customThe reaction mixture is evaporated down
- extractionthe residue is extracted between water and ethyl acetate
- customThe organic phase is dried
- filtrationthe desiccant is filtered off
- customthe filtrate is evaporated down
- customThe purification
Sources & evidence
- ORD record
- ord-42b7a55b249945728f4a1ce3ad7951fc
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07592373B2
Reaction notes
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