Sodium Carbonate → HCID 15008310, compound

HRID 1460955Notes

Reaction equation

HRID 1460955 reaction equation
C(O)(=O)/C=C\C(O)=O.[CH3:9][N:10]1[CH2:15][CH2:14][C:13](=[CH2:16])[CH2:12][CH2:11]1.[Br:17][C:18](Br)=[N:19][OH:20].C(=O)([O-])[O-].[Na+].[Na+]>C(=O)(O)[O-].[Na+]>[Br:17][C:18]1[CH2:16][C:13]2([CH2:14][CH2:15][N:10]([CH3:9])[CH2:11][CH2:12]2)[O:20][N:19]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27632191-bromo-N-hydroxymethanecarbonimidoyl bromideHCID 67948115HCID 67948115, compound

Product 1

HCID 15008310HCID 15008310, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1-methyl-4-methlenepiperidine maleate (1.8 g, 0.0081 mol) in saturated sodium bicarbonate (50 mL) was added dibromoformaldoxime (4.94 g, 0.0244 mol) portionwise. The reaction was stirred at room temperature for 1.5 hours. Additional sodium carbonate was added and then the reaction mixture was extracted with chloroform. The extract was dried(MgSO4) and the solvent was evaporated. The residue was purified by flash chromatography on silica gel and elution with ammoniated CHCl3 /EtOAc/MeOH (2/2/1) to give an oil (0.67 g) which solidified. The solid was dissolved in ether and filtered from the insolubles. The filtrate was acidified with maleic acid and the precipitated solid was recrystallized from EtoAc/Et2O to give the bromo derivative as the maleate salt, mp. 159°-160.5° C.

Workup

  1. extractionthe reaction mixture was extracted with chloroform
  2. customthe solvent was evaporated
  3. customThe residue was purified by flash chromatography on silica gel and elution with ammoniated CHCl3 /EtOAc/MeOH (2/2/1)

Sources & evidence

ORD record
ord-ebbc21ad534e472288118debeb67c07c
Source dataset
uspto-grants-1991_12
Patent number
US05073560

Reaction notes

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