Potassium Iodide → HCID 10198826, compound

HRID 2186674Notes

Reaction equation

HRID 2186674 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[I-].[K+].Cl[CH:11]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[S:14][CH2:13][CH2:12]1>CC(N(C)C)=O>[S:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH:11]([N:1]2[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 68163Hexahydro-1,4-diazepineHCID 11063100HCID 11063100, compound

Product 1

HCID 10198826HCID 10198826, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
60 °C

Procedure

A 100 ml 3-necked flask equipped with a condenser, addition funnel and magnetic stirring bar and under a nitrogen atmosphere was charged with a solution of homopiperazine (3.0 g; 30.5 mmol) in DMAC (35 ml). Potassium iodide (300 mg) was added followed by the addition of a solution of 4-chloro-3,4-dihydro-2H-benzothiopyran (1.15 g; 6.1 mmol) in DMAC (15 ml). This solution was then heated in an oil bath at 60° C. overnight. The reaction mixture was partitioned between water and ethyl acetate, washed with brine and dried with magnesium sulphate. Filtration and evaporation of solvent gave a yellow oil (1.15 g) which exhibited a satisfactory proton nmr spectrum (300 MHz, CDCl3). This material was used without further purification.

Workup

  1. customA 100 ml 3-necked flask equipped with a condenser, addition funnel and magnetic stirring bar and under a nitrogen atmosphere
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. washwashed with brine
  4. dry with materialdried with magnesium sulphate
  5. filtrationFiltration and evaporation of solvent

Sources & evidence

ORD record
ord-476cd91aced844b181274070ed138c38
Source dataset
uspto-grants-2002_06
Patent number
US06407093B1

Reaction notes

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