Sodium Methoxide → 2-(2-Methoxyethyl)-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]piperazine

HRID 518822Notes

Reaction equation

HRID 518822 reaction equation
[CH3:1][O-].[Na+].CS([O:8][CH2:9][CH2:10][CH:11]1[CH2:16][N:15]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([O:26][CH:27]([CH3:29])[CH3:28])[CH:18]=2)[CH2:14][CH2:13][N:12]1[CH3:30])(=O)=O>CO>[CH3:1][O:8][CH2:9][CH2:10][CH:11]1[CH2:16][N:15]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([O:26][CH:27]([CH3:29])[CH3:28])[CH:18]=2)[CH2:14][CH2:13][N:12]1[CH3:30]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 866979872-{1-Methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]piperazin-2-yl}ethyl methanesulfonate

Product 1

HCID 866979882-(2-Methoxyethyl)-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]piperazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

51.1 mg of sodium methoxide are added to a solution of 2-{1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]piperazin-2-yl}ethyl methanesulfonate in 3 ml of methanol. The reaction medium is stirred for 10 minutes at ambient temperature and then 30 minutes at 90° C. in a microwave (CEM). The reaction medium is concentrated to dryness under reduced pressure, and taken up with water and ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated. Purification is carried out by flash chromatography on silica gel (40-63 microns), elution being carried out with a mixture of dichloromethane and methanol (100/0) to (80/20). 100 mg of 2-(2-methoxyethyl)-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]piperazine are obtained in the form of a yellow oil.

Workup

  1. custom30 minutes
  2. customat 90° C.
  3. concentrationThe reaction medium is concentrated to dryness under reduced pressure
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification
  8. washis carried out by flash chromatography on silica gel (40-63 microns), elution
  9. additionbeing carried out with a mixture of dichloromethane and methanol (100/0) to (80/20)

Sources & evidence

ORD record
ord-ba426225afc34c738ac4ab408f87a145
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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