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

HRID 1079395Notes

Reaction equation

HRID 1079395 reaction equation
[ClH:1].Cl.[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=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:5]=[CH:6][C:7]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:8][CH:9]=2)[CH2:21][CH2:20]1)(=[O:18])[CH3:17]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 122563N-Acetyl-4-piperidoneHCID 5003444Sodium cyanoborohydrideHCID 233669404-(Piperidin-1-yl)aniline dihydrochloride

Product 1

HCID 233669781-Acetyl-4-[4-(piperidin-1-yl)phenylamino]piperidine dihydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of N-(4-aminophenyl)piperidine dihydrochloride obtained in Example 17 and 1-acetyl-4-piperidone (0.70 g) in methanol (10 ml) was added sodium cyano borohydride (0.63 g), followed by stirring at room temperature for 5 hours. To the mixture was added ethyl acetate ester (20 ml) and water (30 ml). After the organic layer was dried over anhydrous sodium sulfate, to the solution was added 6N solution of hydrogen chloride in dioxane (2 ml) and the solvent was distilled off. The residue was recrystallized from ethanol to obtain colorless crystals, m.p. 187°-193° C.

Workup

  1. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate, to the solution
  2. additionwas added 6N solution of hydrogen chloride in dioxane (2 ml)
  3. distillationthe solvent was distilled off
  4. customThe residue was recrystallized from ethanol
  5. customto obtain colorless crystals, m.p. 187°-193° C.

Sources & evidence

ORD record
ord-b29ba32005c44275b8f3f5cd1278e0fa
Source dataset
uspto-grants-1996_12
Patent number
US05580883

Reaction notes

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