2-(Chloromethyl)-2,3-dihydro-1,4-benzodioxin → HCID 15541330, compound

HRID 1837499Notes

Reaction equation

HRID 1837499 reaction equation
Cl[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1.[N+:13]([C:16]1[CH:17]=[C:18]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14].C(=O)([O-])O.[K+]>CCCCC(=O)C>[O:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4][CH:3]1[CH2:2][N:25]1[CH2:26][CH2:27][N:22]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=2)[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 953202-(Chloromethyl)-2,3-dihydro-1,4-benzodioxinHCID 516893Potassium BicarbonateHCID 27602161-(3-Nitrophenyl)piperazine

Product 1

HCID 15541330HCID 15541330, compound

Reagents, catalysts & solvents 1

HCID 115832-HexanoneSolvent

Procedure

A solution of 54.2 mmol (10 g) of 2-chloromethyl-2,3-dihydro-1,4-benzodioxin, 54.2 mmol (9.2 g) of 3-nitrophenylpiperazine and 6 g of potassium hydrogen carbonate in 100 ml of methyl-4-pentanone is heated at reflux for 72 hours. After cooling, the reaction mixture is concentrated. The residue is taken up in 200 ml of water and extracted with 200 ml of dichloromethane. The organic phase is dried over magnesium sulphate, concentrated and purified by chromatography on silica gel, using as eluant a 99/1/0.1 dichloromethane/methanol/ammonium hydroxide mixture, to yield the expected product.

Workup

  1. temperatureat reflux for 72 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture is concentrated
  4. extractionextracted with 200 ml of dichloromethane
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. concentrationconcentrated
  7. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-c8f8cb3f02554c5193ea37b91a535d0a
Source dataset
uspto-grants-2004_08
Patent number
US06784183B2

Reaction notes

Loading…