Potassium Carbonate → 1-(3-Methoxy-4-nitrophenyl)piperidin-4-ol

HRID 1014195Notes

Reaction equation

HRID 1014195 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[OH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([N:17]2[CH2:18][CH2:19][CH:14]([OH:13])[CH2:15][CH2:16]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 3

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

Product 1

HCID 259188601-(3-Methoxy-4-nitrophenyl)piperidin-4-olYield 99%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 4-fluoro-2-(methyloxy)-1-nitrobenzene (7.52 g, 44 mmol), 4-hydroxypiperidine (4.45 g, 44 mmol) and potassium carbonate in 100 mL DMSO was stirred for 72 h. The reaction was diluted with water and extracted twice with Ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, and concentrated to give 1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinol (10.9 g, 99% yield). 1H NMR (400 MHz, d6-DMSO) δ 7.84 (d, J=9.2 Hz, 1H), 6.54 (d, J=9.6 Hz, 1H), 6.46 (s, 1H), 4.73 (d, J=4.4 Hz, 1H), 3.86 (s, 3H), 3.80-3.69 (m, 3H), 3.18-3.12 (m, 2H), 1.79-1.76 (m, 2H), 1.42-1.34 (m, 2H).

Workup

  1. extractionextracted twice with Ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4f3bed9c34dd45d3b46348f3fd703097
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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