Sodium Carbonate → HCID 18766138, compound

HRID 19753Notes

Reaction equation

HRID 19753 reaction equation
[CH3:1][NH:2][O:3][CH2:4][CH:5](O)[CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C([O-])([O-])=O.[Na+].[Na+].Cl.[CH3:21][N:22]([CH3:32])[C:23](Cl)=[N:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)(Cl)Cl>[CH3:21][N:22]([CH3:32])[C:23]([N:2]([CH3:1])[O:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[N:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 18766168HCID 18766168, compoundHCID 18766269HCID 18766269, compound

Product 1

HCID 18766138HCID 18766138, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

344 mg (2.0 mmole) 1-methylaminooxy-2-hydroxy-3-(1-piperidinyl)-propane was dissolved in chloroform and 220 mg of Na2CO3 was added, then a solution of 438 mg (2.0 mmole) of N,N-dimethyl-N′-phenyl-chloroformamidine hydrochloride in 3 ml of chloroform was added dropwise. After 8 hours the solid state was filtered and the filtrate was evaporated. This residue was dissolved in ethyl acetate and the product was extracted by addition of HCl solution (pH=1) to water. The aqueous phase was made alkaline then by addition of 2N NaOH solution to pH=11, and extracted with ethyl acetate. The organic phase was evaporated, and the further purification was made by column chromatography to give the title compound as a yellow oil.

Workup

  1. filtrationAfter 8 hours the solid state was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThis residue was dissolved in ethyl acetate
  4. extractionthe product was extracted by addition of HCl solution (pH=1) to water
  5. additionby addition of 2N NaOH solution to pH=11
  6. extractionextracted with ethyl acetate
  7. customThe organic phase was evaporated
  8. customthe further purification

Sources & evidence

ORD record
ord-e918f875a607444f813bc939024be72a
Source dataset
uspto-grants-2010_06
Patent number
US07745465B2

Reaction notes

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