Potassium Iodide → 2,2-Dimethyl-3-(piperidin-1-yl)propan-1-ol

HRID 1867442

Reaction equation

HRID 1867442 reaction equation
Br[CH2:2][C:3]([CH3:7])([CH3:6])[CH2:4][OH:5].[NH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>CC(N(C)C)=O>[CH3:6][C:3]([CH3:7])([CH2:2][N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 1425013-Bromo-2,2-dimethyl-1-propanol

Product 1

HCID 2960142,2-Dimethyl-3-(piperidin-1-yl)propan-1-olYield 18.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 3.00 g (17.96 mmol) of 3-bromo-2,2-dimethyl-propan-1-ol, 17.78 ml (179.59 mmol) of piperidine, 2.48 g (17.96 mmol) of K2CO3 and 2.69 g (17.96 mmol) of potassium iodide in 20 ml of DMA were stirred at 70° C. for 20 h. After filtration and evaporation of the solvents, the crude product was dissolved in diluted aqueous HCl solution and washed with EtOAc (3×). The aqueous phase was basified with KHCO3 and some drops of 1N NaOH and extracted with EtOAc (3×). The organic phase was dried (Na2SO4) and evaporated to give 0.57 g (18%) of the title compound as yellow liquid. MS: 172.0 (MH+).

Workup

  1. filtrationAfter filtration and evaporation of the solvents
  2. dissolutionthe crude product was dissolved in diluted aqueous HCl solution
  3. washwashed with EtOAc (3×)
  4. extractionsome drops of 1N NaOH and extracted with EtOAc (3×)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-b514df5563304e91b0b3c788c0279966
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Linked notes

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