Water → HCID 18430905, compound

HRID 1278613Notes

Reaction equation

HRID 1278613 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH2:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl:20][CH2:21][CH2:22][O:23][C:24](Cl)=[O:25].O>O1CCCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:24](=[O:25])[O:23][CH2:22][CH2:21][Cl:20])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 123052-Chloroethyl chloroformateHCID 14798Sodium HydroxideHCID 31492693-(4-benzylpiperazin-1-yl)propan-1-amine

Product 1

HCID 18430905HCID 18430905, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-(4-benzyl-1-piperazinyl)propylamine (2.01 g/8.61 mmol) in tetrahydrofuran (15 ml) were added 2 N NaOH (6.5 ml/13.0 mmol) and 2-chloroethylchloroformate (1.38 ml/12.9 mmol), and the mixture was stirred for 1 d. Water (50 ml) was added to the mixture and the whole was extracted with ethyl acetate (50 ml). The extract was 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.

Workup

  1. extractionthe whole was extracted with ethyl acetate (50 ml)
  2. washThe extract was washed with brine (50 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (NH2 gel/dichloromethane)
  7. customto give a colorless oil

Sources & evidence

ORD record
ord-1afabffae04a453bb66f5b5f31916494
Source dataset
uspto-grants-2002_09
Patent number
US06444677B2

Reaction notes

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