Potassium Iodide → Ethyl 4-(diphenylmethoxy)-1-piperidinebutanoate

HRID 1182080Notes

Reaction equation

HRID 1182080 reaction equation
[CH:1]([O:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[I-].[K+].[CH2:28]([O:30][C:31](=[O:36])[CH2:32][CH2:33][CH2:34]Cl)[CH3:29]>C(C(C)=O)C(C)C>[CH2:28]([O:30][C:31](=[O:36])[CH2:32][CH2:33][CH2:34][N:18]1[CH2:19][CH2:20][CH:15]([O:14][CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:16][CH2:17]1)[CH3:29]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 18474Ethyl 4-chlorobutyrateHCID 516892Sodium BicarbonateHCID 30175844-Benzhydryloxypiperidine

Product 1

HCID 10429946Ethyl 4-(diphenylmethoxy)-1-piperidinebutanoateYield 66%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To 28 mL of methyl isobutyl keton (MIBK) was added 4-(benzhydryloxy)piperidine (1.5 g), NaHCO3 (1.42 g), potassium iodide (catalyst), and ethyl-4-chlorobutyrate (1.2 mL). The resulting mixture was refluxed for 4 hrs. The resulting mixture was cooled, and concentrated under reduced pressure. The resultant solution was then extracted by using water and chloroform. An organic solution layer was dehydrated over magnesium sulfate, filtered, and concentrated under reduced pressure. The column chromatography was performed thereon, thereby obtaining crude yellowish liquid product (1.41 g, 66% yield) of the title.

Workup

  1. temperatureThe resulting mixture was refluxed for 4 hrs
  2. temperatureThe resulting mixture was cooled
  3. concentrationconcentrated under reduced pressure
  4. extractionThe resultant solution was then extracted
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-945b470a27be46bcafb0203c7b96a258
Source dataset
uspto-grants-2007_10
Patent number
US07288552B2

Reaction notes

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