Potassium Carbonate → 4-(3-Chlorophenoxy)piperidine

HRID 463306Notes

Reaction equation

HRID 463306 reaction equation
CNCCCC1(C2C=CC(F)=CC=2)OCCO1.C(=O)([O-])[O-].[K+].[K+].BrCC([N:28]1[CH2:33][CH2:32][CH:31]([O:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[CH:36]=2)[CH2:30][CH2:29]1)=O.C(=O)(O)[O-].[Na+].C(O)(=O)C(O)=O.FC1C=CC(C2(CCCN(CC(N3CCC(OC4C=CC=C(Cl)C=4)CC3)=O)C)OCCO2)=CC=1>C(O)C>[Cl:41][C:37]1[CH:36]=[C:35]([CH:40]=[CH:39][CH:38]=1)[O:34][CH:31]1[CH2:30][CH2:29][NH:28][CH2:33][CH2:32]1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 133357082-[3-(Methylamino)propyl]-2-(4-fluorophenyl)-1,3-dioxolaneHCID 20283061N-(2-bromoacetyl)-4-(m-chlorophenoxy)piperidineHCID 202831291-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylaminoacetyl}-4-(3-chlorophenoxy)piperidine oxalate

Product 1

HCID 27353174-(3-Chlorophenoxy)piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of 2-[3-(methylamino)propyl]-2-(4-fluorophenyl)-1,3-dioxolane (7.2 g, 30.0 mmol), potassium carbonate (10.6 g, 76.8 mmol) and 120 ml of ethanol at 0° was added dropwise a solution of N-(2-bromoacetyl)-4-(3-chlorophenoxy)piperidine (11.3 g, 34.0 mmol) in 120 ml of ethanol. The solution was stirred 1 hour at room temperature and at reflux for 1 hour. The mixture was poured into saturated sodium bicarbonate, extracted with methylene chloride, washed with water and dried over magnesium sulfate. Filtration followed by evaporation of the solvent provided an oil. Yield: 11.0 g of 1-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylaminoacetyl}-4-(3-chlorophenoxy)piperidine oxalate. Yield from 4-(3-chlorophenoxy)piperidine: 43%; from N-(2-bromoacetyl)-4-(3-chlorophenoxy)piperidine: 77%.

Workup

  1. temperatureat reflux for 1 hour
  2. extractionextracted with methylene chloride
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration
  6. customfollowed by evaporation of the solvent
  7. customprovided an oil

Sources & evidence

ORD record
ord-36976273ec844bba84cba99274933333
Source dataset
uspto-grants-1985_05
Patent number
US04518713

Reaction notes

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