Potassium Iodide → HCID 178482548, compound

HRID 1162361Notes

Reaction equation

HRID 1162361 reaction equation
Br[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[CH3:17][NH:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1.[I-].[K+]>CN(C=O)C>[CH3:17]/[N:18]=[C:19]1\[S:20][CH:21]=[CH:22][N:23]\1[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 10541625tert-Butyl 4-(2-bromoethyl)piperidine-1-carboxylateHCID 11959081N-methyl-2-Thiazolamine

Product 1

HCID 178482548HCID 178482548, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 4-(2-bromoethyl)-1-piperidinecarboxylate (D. Brundish et al., J. Med. Chem., 42, 4584 (1999); 5.0 g) and 2-methylaminothiazole (O. Kemal et al., J. Chem. Soc. Perkin I, 5, 1569 (1981); 3.9 g) in DMF (50 ml) was added potassium iodide (5.7 g), and mixed at 80° C. for 12 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in chloroform and a saturated aqueous potassium hydrogen carbonate solution. The organic layer was collected by separation, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified with silica gel column to obtain the title compound as a brown oil (1.25 g, 22%).

Workup

  1. additionmixed at 80° C. for 12 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. customThe organic layer was collected by separation
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with silica gel column

Sources & evidence

ORD record
ord-21653e90c22f4829967f96fc069a661e
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

Loading…