Potassium Carbonate → 1-benzyl-N-methylpiperidin-4-amine

HRID 1269775Notes

Reaction equation

HRID 1269775 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([N:20](C)[C:21](=O)C(F)(F)F)[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CO.O>[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([NH:20][CH3:21])[CH2:16][CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 20569912N-(1-benzyl-4-piperidinyl)-2,2,2-trifluoro-N-methylacetamide

Product 1

HCID 41361281-benzyl-N-methylpiperidin-4-amineYield 128.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Potassium carbonate (662 mg, 4.79 mmol) was added to a solution of N-(1-benzyl-4-piperidinyl)-2,2,2-trifluoro-N-methylacetamide (720 mg, 2.40 mmol) in a mixture of methanol (14 ml) and water (2 ml) at room temperature and stirred at 50° C. for 1.5 hours. After the reaction solution was concentrated, a saturated aqueous sodium hydrogencarbonate solution was added thereto, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent, whereby 1-benzyl-N-methylpiperidin-4-amine (629 mg, 100%) was obtained.

Workup

  1. concentrationAfter the reaction solution was concentrated
  2. additiona saturated aqueous sodium hydrogencarbonate solution was added
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent

Sources & evidence

ORD record
ord-6548f60cbc684d6995c2b4f2596b3385
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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