Acetic Acid → HCID 18770447, compound

HRID 479393Notes

Reaction equation

HRID 479393 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([BH3-])#[N:16].[Na+].[CH3:19][NH:20][CH2:21][CH2:22][NH:23][CH3:24].[C:25](O)(=O)[CH3:26].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:20]([CH3:19])[CH2:21][CH2:22][N:23]([CH:11]2[CH2:12][CH2:13][N:16]([CH2:15][C:26]3[CH:25]=[CH:4][CH:3]=[CH:2][CH:1]=3)[CH2:9][CH2:10]2)[CH3:24])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 192201-Benzyl-4-piperidoneHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18770447HCID 18770447, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After 1-benzyl-4-piperidone (5.00 g; 26 mmol) and sodium cyanoborohydride (1.25 g; 20 mmol) were added to a solution of N,N′-dimethylethylenediamine (785 mg; 8.9 mmol) in methanol (20 ml) under ice cooling. The ice bath was removed, and acetic acid (2.5 ml; 44 mmol) was added to the solution, and the mixture was stirred for 15 minutes. Potassium carbonate (3 g; 22 mmol) and a saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture to conduct extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel, thereby obtaining 955 mg (yield: 25%) of N,N′-bis(1-benzyl-4-piperidinyl)-N,N′-dimethylethylenediamine as a colorless oil.

Workup

  1. customThe ice bath was removed
  2. extractionextraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8d985984869c4cb5b19f4f5d8417119a
Source dataset
uspto-grants-2003_11
Patent number
US06645957B2

Reaction notes

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