Potassium Carbonate → HCID 86698012, compound

HRID 518859Notes

Reaction equation

HRID 518859 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH:12]([CH3:14])[CH3:13])[CH:3]=1.[CH3:15][N:16]1[C:20]2([CH2:24][CH2:23][NH:22][CH2:21]2)[CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[CH3:15][N:16]1[C:20]2([CH2:24][CH2:23][N:22]([C:2]3[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH:12]([CH3:14])[CH3:13])[CH:3]=3)[CH2:21]2)[CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 106318324-Fluoro-2-isopropoxy-1-nitrobenzeneHCID 529881151-Methyl-1,7-diazaspiro[4.4]nonane

Product 1

HCID 86698012HCID 86698012, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 1.42 g of 4-fluoro-1-nitro-2-(propan-2-yloxy)benzene, 1.0 g of 1-methyl-1,7-diazaspiro[4,4]nonane and 1.48 g of potassium carbonate in 10 ml of DMSO is stirred at ambient temperature overnight. The mixture is diluted with 160 ml of water and extracted three times with 100 ml of ethyl acetate. The organic phases are dried over magnesium sulfate and concentrated under vacuum. The yellow oily residue is purified on silica, with an elution gradient with dichloromethane/methanol (100/0 then 90/10), so as to obtain 160 mg of 1-methyl-7-[4-nitro-3-(propan-2-yloxy)phenyl]-1,7-diazaspiro[4.4]nonane in the form of an orangey-coloured oil.

Workup

  1. extractionextracted three times with 100 ml of ethyl acetate
  2. dry with materialThe organic phases are dried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe yellow oily residue is purified on silica, with an elution gradient with dichloromethane/methanol (100/0

Sources & evidence

ORD record
ord-8d2076da8abf4742b6dc55e27a221b8e
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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