Water → 1-(3-Methoxy-4-nitrophenyl)piperidin-4-ol

HRID 1256001Notes

Reaction equation

HRID 1256001 reaction equation
C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([O:17][CH3:18])[CH:9]=1.[NH:19]1[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]1.O>CS(C)=O>[CH3:18][O:17][C:10]1[CH:9]=[C:8]([N:19]2[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]2)[CH:13]=[CH:12][C:11]=1[N+:14]([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 259188601-(3-Methoxy-4-nitrophenyl)piperidin-4-olYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

Potassium carbonate (4.85 g, 35.06 mmol) was added to a stirring solution of 4-fluoro-2-methoxy-1-nitrobenzene (5.0 g, 29.22 mmol) and piperidin-4-ol (2.96 g, 29.22 mmol) in DMSO (20 mL) and the reaction mixture was heated at 90° C. for 1 h. The reaction mixture was allowed to cool to RT and water (200 mL) was added. The resultant precipitates were collected by vacuum filtration and washed with water and Et2O to give the title product as a yellow solid (7.0 g, 95%).

Workup

  1. temperatureto cool to RT
  2. customThe resultant precipitates
  3. filtrationwere collected by vacuum filtration
  4. washwashed with water and Et2O

Sources & evidence

ORD record
ord-cf53eaacc55a46198215d6dbd4cd5521
Source dataset
uspto-grants-2013_06
Patent number
US08461170B2

Reaction notes

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