2-(Chloromethyl)-2,3-dihydro-1,4-benzodioxin → HCID 15541331, compound

HRID 1795208Notes

Reaction equation

HRID 1795208 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-])=O.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[CH2:24][CH2:23][N:22]([C:18]2[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=2)[NH2:13])[CH2:27][CH2:26]1

Participants

5

Reactant 3

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

Product 1

HCID 15541331HCID 15541331, 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-94fc9a147e76413cb18075da90909d92
Source dataset
uspto-grants-2006_04
Patent number
US07026357B2

Reaction notes

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