Potassium Carbonate → HCID 83013400, compound

HRID 518852Notes

Reaction equation

HRID 518852 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([O:11][CH:12]([CH3:14])[CH3:13])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[NH2:15][CH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[CH:12]([O:11][C:5]1[CH:4]=[C:3]([NH:15][CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:2]=[CH:7][C:6]=1[N+:8]([O-:10])=[O:9])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 4192234-AminotetrahydropyranHCID 53255709HCID 53255709, compound

Product 1

HCID 83013400HCID 83013400, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 0.75 g of 5-fluoro-1-nitro-2-(propan-2-yloxy)benzene, 0.42 g of 4-aminotetrahydropyran and 0.8 g of potassium carbonate in 6 ml of DMSO is stirred at 50° C. overnight. The mixture is diluted with 100 ml of water and extracted three times with 50 ml of ethyl acetate. The organic phases are combined and then dried over magnesium sulfate and concentrated to dryness under reduced pressure. The residue is purified by chromatography on a 50 g silica column, elution being carried out with a dichloromethane/methanol (95/5 v/v) mixture, so as to obtain 0.69 g of (3-isopropoxy-4-nitrophenyl)(tetrahydropyran-4-yl)amine in the form of a yellow foam.

Workup

  1. extractionextracted three times with 50 ml of ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe residue is purified by chromatography on a 50 g silica column, elution

Sources & evidence

ORD record
ord-6b570f6c477a4d00847eee344798ef09
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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