Sodium Iodide → Methyl 4-(3,4-dichlorophenoxy)-1-piperidinebutanoate

HRID 915539

Reaction equation

HRID 915539 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 107604Methyl 4-bromobutyrateHCID 37320424-(3,4-Dichlorophenoxy)piperidine

Product 1

HCID 69417722Methyl 4-(3,4-dichlorophenoxy)-1-piperidinebutanoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-(3,4-Dichlorophenoxy)piperidine (4.15 g) was dissolved in acetone (80 ml). Potassium carbonate (2.42 g), sodium iodide (0.49 g) and then methyl 4-bromobutyrate (1.95 ml) were added and the mixture was stirred for 42 h. The solvent, was evaporated and the residue was partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate. The organic phases were dried (MgSO4), filtered and evaporated and the residue was chromatographed eluting with ethyl acetate: triethylamine (99:1) to give the subtitle compound (4.52 g).

Workup

  1. customThe solvent, was evaporated
  2. customthe residue was partitioned between water and ethyl acetate
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue was chromatographed
  8. washeluting with ethyl acetate: triethylamine (99:1)

Sources & evidence

ORD record
ord-6e42b245ec7a42478dab5d862e88db9b
Source dataset
uspto-grants-2007_09
Patent number
US07265227B2

Linked notes

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