Ethyl Acetate → 1-Acetyl-4-[3-(piperidin-1-yl)phenylamino]-piperidine dihydrochloride

HRID 1079399Notes

Reaction equation

HRID 1079399 reaction equation
[ClH:1].Cl.[NH2:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.[C:16]([N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)(=[O:18])[CH3:17].C([BH3-])#N.[Na+].C(OCC)(=O)C>CO.O>[ClH:1].[ClH:1].[C:16]([N:19]1[CH2:24][CH2:23][CH:22]([NH:3][C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[CH:5]=2)[CH2:21][CH2:20]1)(=[O:18])[CH3:17]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 122563N-Acetyl-4-piperidoneHCID 5003444Sodium cyanoborohydrideHCID 233669441-(3-Aminophenyl)piperidine dihydrochloride

Product 1

HCID 233669001-Acetyl-4-[3-(piperidin-1-yl)phenylamino]-piperidine dihydrochlorideYield 132.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of N-(3-aminophenyl)piperidine dihydrochloride (3.73 g) and 1-acetyl-4-piperidone (2.1 g) in methanol (30 ml) was added sodium cyano borohydride (1.9 g), followed by stirring at room temperature for 5 hours. To the mixture were added ethyl acetate ester (20 ml) and water (30 ml), the organic layer was dried over anhydrous sodium sulfate and then the solvent was distilled off. The residual oily compound was separated and purified by silica gel column chromatography (developing solvent: ethyl acetate ester). The oily compound was dissolved in dioxane (10 ml) and to the mixture was added 6N solution of hydrogen chloride in dioxane (2 ml). Then, the solvent was removed to obtain a colorless amorphous solid (3.7 g).

Workup

  1. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  2. distillationthe solvent was distilled off
  3. customThe residual oily compound was separated
  4. custompurified by silica gel column chromatography (developing solvent: ethyl acetate ester)
  5. dissolutionThe oily compound was dissolved in dioxane (10 ml) and to the mixture
  6. additionwas added 6N solution of hydrogen chloride in dioxane (2 ml)
  7. customThen, the solvent was removed

Sources & evidence

ORD record
ord-3f0c13b8f65045b798b39ce173b37ba1
Source dataset
uspto-grants-1996_12
Patent number
US05580883

Reaction notes

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