Sodium → HCID 18430883, compound

HRID 1278612Notes

Reaction equation

HRID 1278612 reaction equation
[Na].[CH2:2]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][S:19]([CH2:22][CH2:23][CH2:24]Cl)(=[O:21])=[O:20])[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)C>[CH2:2]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][N:18]2[CH2:24][CH2:23][CH2:22][S:19]2(=[O:21])=[O:20])[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 18430934HCID 18430934, compound

Product 1

HCID 18430883HCID 18430883, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium (0.23 g/10.0 mmol) was added to ethanol (20 ml). To the resulting solution was added N-[3-(4-benzyl-1-piperazinyl)propyl]-3-chloro-1-propanesulfonamide in ethanol (20 ml) and the mixture was stirred for 1 day at reflux temperature. The solvent was removed in vacuo and the residue was diluted with dichloromethane (50 ml) and water (50 ml). The aqueous layer was extracted with dichloromethane (50 ml). The combined extracts were washed with brine (50 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (NH2 gel/dichloromethane) to give a colorless oil (0.60 g/21%).

Workup

  1. temperatureat reflux temperature
  2. customThe solvent was removed in vacuo
  3. additionthe residue was diluted with dichloromethane (50 ml) and water (50 ml)
  4. extractionThe aqueous layer was extracted with dichloromethane (50 ml)
  5. washThe combined extracts were washed with brine (50 ml)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (NH2 gel/dichloromethane)
  10. customto give a colorless oil (0.60 g/21%)

Sources & evidence

ORD record
ord-519b93e1e339480a9fce67f427fee519
Source dataset
uspto-grants-2002_09
Patent number
US06444677B2

Reaction notes

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