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Sodium Carbonate → HCID 18403745, compound

HRID 1017687
Notes
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Reaction equation

HRID 1017687 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([NH:14][CH3:15])=[O:13])[CH:6]=O.[N:16]1([C:22]2[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[CH:24][CH:23]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][N:19]2[CH2:18][CH2:17][N:16]([C:22]3[CH:23]=[CH:24][C:25]([C:28](=[O:30])[CH3:29])=[CH:26][CH:27]=3)[CH2:21][CH2:20]2)[CH:8]=[CH:9][C:10]=1[O:11][C:12]([NH:14][CH3:15])=[O:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 97269Piperazin-4-ylacetophenoneHCID 4064704HCID 4064704, compoundHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18403745HCID 18403745, compound

Reagents, catalysts & solvents 1

HCID 11
1,2-Dichloroethane
Solvent

Procedure

To a solution of 3-methoxy-4-(methylaminocarbonyloxy)benzaldehyde (1.0 g) in 1,2-dichloroethane (20 ml) was added 4′-piperazinoacetophenone (0.98 g), followed by sodium triacetoxyborohydride (1.53 g), with stirring. The reaction mixture was stirred overnight at ambient temperature, poured into saturated sodium carbonate solution (75 ml) and extracted with dichloromethane. The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was dissolved in dichloromethane and flash chromatographed (silica gel and dichloromethane), eluting with the same solvent system, followed by 1% methanol:dichloromethane. The appropriate fractions were combined and concentrated. The residue was recrystallized from ethyl acetate to give product, mp 120-123° C.

Workup

  1. stirringThe reaction mixture was stirred overnight at ambient temperature
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. dissolutionThe residue was dissolved in dichloromethane
  8. customflash chromatographed (silica gel and dichloromethane)
  9. washeluting with the same solvent system
  10. concentrationconcentrated
  11. customThe residue was recrystallized from ethyl acetate
  12. customto give product, mp 120-123° C.

Sources & evidence

ORD record
ord-8d3362157ddf4ee68b8f7abf54ef26f0
Source dataset
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06479495B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes