1-Methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]pyridinium iodide → HCID 68360001, compound

HRID 518796

Reaction equation

HRID 518796 reaction equation
[I-].[CH3:2][N+:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([O:18][CH:19]([CH3:21])[CH3:20])[CH:10]=2)=[CH:5][CH:4]=1.[H][H]>CO.O.[Pt]=O>[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([O:18][CH:19]([CH3:21])[CH3:20])[CH:10]=2)[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 866979641-Methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]pyridinium iodideHCID 178418361HCID 178418361, compound

Product 1

HCID 68360001HCID 68360001, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 86587499Platinum oxide monohydrateCatalystHCID 887MethanolSolvent

Procedure

A solution of 10 g of 1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]pyridinium iodide in 280 ml of methanol is hydrogenated in an autoclave on 2.9 g of platinum oxide hydrate, at a hydrogen pressure of 15 bar and at ambient temperature for 4 h. The catalyst is removed by filtration on Clarcel and the mixture is concentrated under vacuum. The residue is taken up in 200 ml of ethyl acetate and washed with 200 ml of 1M sodium hydroxide and then with a saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated under vacuum, so as to obtain 6.0 g of 4-(1-methylpiperidin-4-yl)-2-(propan-2-yloxy)aniline.

Workup

  1. customThe catalyst is removed by filtration on Clarcel
  2. concentrationthe mixture is concentrated under vacuum
  3. washwashed with 200 ml of 1M sodium hydroxide
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-946ca97885874ef1b5b284a4e52a64f0
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Linked notes

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