Potassium Iodide → HCID 9816704, compound

HRID 2186673Notes

Reaction equation

HRID 2186673 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[I-].[K+].Cl[CH:12]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[S:15][CH2:14][CH2:13]1>CC(N(C)C)=O>[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][N:5]([CH:12]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[S:15][CH2:14][CH2:13]2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 2283491-MethylhomopiperazineHCID 11063100HCID 11063100, compound

Product 1

HCID 9816704HCID 9816704, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

A 25 ml 3-necked flask equipped with a condenser and magnetic stirring bar and under a nitrogen atmosphere was charged with a solution of N-methylhomopiperazine (0.35 ml; 2.81 mmol) in DMAC (10 ml). Potassium iodide (0.1 g) was added followed by the addition of 4-chloro-3,4-dihydro-2H-benzothiopyran (0.20 g; 1.2 mmol). This solution was then heated at 60° C. overnight, cooled, and partitioned between water and ethyl acetate which was washed with brine and dried with magnesium sulphate. Filtration and evaporation of solvent gave a yellow oil which was distilled by kugelrohr to give the title compound as an oil (0.31 g), bp (air bath temperature) 130-140° C. at 100 mtorr; essentially homogeneous by tlc (silica gel, 89:10:1 CH2Cl2:CH3OH:NH4OH), Rf 0.46; 1H nmr δ2.37 (s, 3H), 3.82-3.87 (m, 1H), 6.98-7.34 (m, 3H), 7.69-7.71 (d, 1H).

Workup

  1. customA 25 ml 3-necked flask equipped with a condenser and magnetic stirring bar and under a nitrogen atmosphere
  2. temperaturecooled
  3. custompartitioned between water and ethyl acetate which
  4. washwas washed with brine
  5. dry with materialdried with magnesium sulphate
  6. filtrationFiltration and evaporation of solvent
  7. customgave a yellow oil which
  8. distillationwas distilled by kugelrohr

Sources & evidence

ORD record
ord-09f6e3aaa2ac424ea75e1f4fa9b54970
Source dataset
uspto-grants-2002_06
Patent number
US06407093B1

Reaction notes

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