Sodium Hydroxide → HCID 18180077, compound

HRID 1358941Notes

Reaction equation

HRID 1358941 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[N:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1.[N+:17]([O-])([O-:19])=[O:18].[K+].[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[C:4]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[C:5]([CH3:9])[C:6]([N+:17]([O-:19])=[O:18])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 18180146HCID 18180146, compound

Product 1

HCID 18180077HCID 18180077, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
27.5 °C

Procedure

A solution of 1-(2-methoxy-6-methylphenyl)-4-methylpiperazine (D29) (6.2 g, 28 mmol) in concentrated sulfuric acid (50 ml) was treated portionwise with potassium nitrate (3.3 g, 33 mmol) over 5 mins, maintaining the temperature at 25-30° C. The mixture was stirred overnight at room temperature, then added to ice, and basified with 40% sodium hydroxide solution. The mixture was extracted with dichloromethane and the organic phase was dried (Na2SO4) and evaporated under reduced pressure to give crude compound. Purification by chromatography on silica gel eluting with methanol and dichloromethane afforded the title compound (D30) (4.56 g, 61%) MH+=266.

Workup

  1. additionadded to ice
  2. extractionThe mixture was extracted with dichloromethane
  3. dry with materialthe organic phase was dried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customto give crude compound
  6. customPurification by chromatography on silica gel eluting with methanol and dichloromethane

Sources & evidence

ORD record
ord-00349f94580e4817b5a166d24d7f268c
Source dataset
uspto-grants-2003_07
Patent number
US06599904B2

Reaction notes

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