Sodium hydride → HCID 18430906, compound

HRID 1278614Notes

Reaction equation

HRID 1278614 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:25])[O:21][CH2:22][CH2:23]Cl)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CN(C)C=O>[CH2:3]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]2[CH2:23][CH2:22][O:21][C:20]2=[O:25])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 18430905HCID 18430905, compound

Product 1

HCID 18430906HCID 18430906, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Sodium hydride(60% in oil, 0.5 g/12.5 mmol) was added to a solution of 2-chloroethyl 3-(4-benzyl-1-piperazinyl)propylcarbamate in dimethylformamide(20 ml) and stirred for 1 day at 80° C. 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 (1.40 g/54%).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with dichloromethane (50 ml) and water (50 ml)
  3. extractionThe aqueous layer was extracted with dichloromethane (50 ml)
  4. washThe combined extracts were washed with brine (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (NH2 gel/dichloromethane)
  9. customto give a colorless oil (1.40 g/54%)

Sources & evidence

ORD record
ord-88dc51fbe36a4eb2a93564b4ad9f98fa
Source dataset
uspto-grants-2002_09
Patent number
US06444677B2

Reaction notes

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