Sodium Hydroxide → HCID 18435932, compound

HRID 351344Notes

Reaction equation

HRID 351344 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.[OH-].[Na+]>C(O)C>[CH3:11][N:12]1[CH2:17][CH2:16][C:15]2[N:1]=[C:2]3[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:3]3=[CH:4][C:14]=2[CH2:13]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 740491-Methyl-4-piperidoneHCID 111477482,4-Diaminobenzaldehyde

Product 1

HCID 18435932HCID 18435932, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,4-diaminobenzaldehyde (1.00 g, 7.34 mmol), 1-methyl-4-piperidinone (1.08 ml, 8.81 mmol) and 4N aqueous sodium hydroxide solution (11 ml) in ethanol (70 ml) was stirred at 60° C. for 16 hrs, and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, washed with aqueous potassium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The obtained crude product was purified by NH-silica gel chromatography (elute solvent; ethyl acetate) and treated with ethyl acetate-isopropyl ether (1:5) to give the title compound (666 mg) as a powder.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with aqueous potassium carbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe obtained crude product
  6. customwas purified by NH-silica gel chromatography (elute solvent; ethyl acetate)
  7. additiontreated with ethyl acetate-isopropyl ether (1:5)

Sources & evidence

ORD record
ord-a5b8d1b7fa7d42ccb532b3b97cc9d00b
Source dataset
uspto-grants-2007_02
Patent number
US07183415B2

Reaction notes

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