Water → 1-(4-Aminophenyl)piperidin-4-ol

HRID 57590Notes

Reaction equation

HRID 57590 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[NH:17]1[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]1.O>CS(C)=O>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([N:17]2[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]2)=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 79341Piperidin-4-ol

Product 1

HCID 167921071-(4-Aminophenyl)piperidin-4-olYield 96.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 1-fluoro-4-nitrobenzene (2.82 g, 20 mmol) and K2CO3 (6.92 g, 50 mmol) in dimethyl sulfoxide (20 mL) was added piperidin-4-ol (2.22 g, 22 mmol) and the reaction was heated to 100° C. for 4 hours. This solution was poured into 200 ml of water and extracted with ethyl acetate (30 mL×3). The organic phase was combined and washed with saturated brine and dried over anhydrous sodium sulfate. The solid was filtered and the filtrate, 10% Pd/C (100 mg) was added and the mixture was stirred under hydrogen atmosphere at ambient temperature overnight. The catalyst was filtered, and the filtrate was concentrated to afford tan solid 3.7 g. MS (m/z): 193 (M+H)+

Workup

  1. extractionextracted with ethyl acetate (30 mL×3)
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe solid was filtered
  5. additionthe filtrate, 10% Pd/C (100 mg) was added
  6. filtrationThe catalyst was filtered
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f70d4ef69e8c4a98836c1440d05443c9
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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