Potassium Carbonate → HCID 59860244, compound

HRID 1014192Notes

Reaction equation

HRID 1014192 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([OH:8])[CH2:3]1.F[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([O:19][CH3:20])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)C.[Cl-].[Na+]>[CH3:20][O:19][C:12]1[CH:11]=[C:10]([N:2]2[CH2:7][CH2:6][CH2:5][C@H:4]([OH:8])[CH2:3]2)[CH:15]=[CH:14][C:13]=1[N+:16]([O-:18])=[O:17]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27792505-Fluoro-2-nitroanisoleHCID 16211918(3S)-Piperidin-3-ol--hydrogen chloride (1/1)

Product 1

HCID 59860244HCID 59860244, compoundYield 78.3%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolventHCID 5234Sodium ChlorideSolvent

Procedure

A solution of (3S)-3-piperidinol hydrochloride (3.00 g, 21.7 mmol, Astatech Inc.), 4-fluoro-2-(methyloxy)-1-nitrobenzene (3.38 g, 19.76 mmol) and potassium carbonate (9.00 g, 65.22 mmol) in dimethylsulfoxide (75 mL) was stirred overnight. The next morning, the reaction was diluted with diethyl ether and saturated aqueous sodium chloride. The ether layer was washed with water, and the combined aqueous layers were subsequently washed twice with diethyl ether. The combined organic layers were dried over sodium sulfate, filtered, taken to a residue under reduced pressure, and purified by chromatography on SiO2 (5% MeOH/CH2CL2) to give (3S)-1-[3-(methyloxy)-4-nitrophenyl]-3-piperidinol as a pale yellow solid (3.90 g, 15.47 mmol, 78% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.59-1.71 (m, 2 H), 1.79 (s, 1 H), 1.86-1.96 (m, J=12.96, 6.41, 6.27, 3.48 Hz, 1 H), 1.96-2.04 (m, 1 H), 3.13-3.24 (m, 2 H), 3.47 (ddd, J=12.59, 6.36, 3.20 Hz, 1 H), 3.66 (dd, J=12.82, 3.48 Hz, 1 H), 3.86-3.92 (m, J=7.44, 3.94, 3.74, 3.74 Hz, 1 H), 3.93 (s, 3 H), 6.34 (d, J=2.56 Hz, 1 H), 6.43 (dd, J=9.34, 2.38 Hz, 1 H), 7.98 (d, J=9.34 Hz, 1 H).

Workup

  1. washThe ether layer was washed with water
  2. washthe combined aqueous layers were subsequently washed twice with diethyl ether
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. custompurified by chromatography on SiO2 (5% MeOH/CH2CL2)

Sources & evidence

ORD record
ord-852a6063d0f744aabf70f987399fdf72
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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