Sodium Hydroxide → HCID 18430934, compound

HRID 1278611Notes

Reaction equation

HRID 1278611 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][CH2:23][S:24](Cl)(=[O:26])=[O:25]>O1CCCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][NH:17][S:24]([CH2:23][CH2:22][CH2:21][Cl:20])(=[O:26])=[O:25])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 154103-Chloropropanesulphonyl chlorideHCID 31492693-(4-benzylpiperazin-1-yl)propan-1-amine

Product 1

HCID 18430934HCID 18430934, 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 (5.6 ml/ 11.2 mmol) and 3-chloropropanesulfonylchloride (2.00 g/11.3 mmol), and the mixture was stirred for 1 day. The reaction mixture was quenched with water (50 ml) 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. customThe reaction mixture was quenched with water (50 ml)
  2. extractionthe whole was extracted with ethyl acetate (50 ml)
  3. washThe extract was washed with brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (NH2 gel/dichloromethane)
  8. customto give a colorless oil

Sources & evidence

ORD record
ord-99e2016b805e4f4d94b7e565237f9589
Source dataset
uspto-grants-2002_09
Patent number
US06444677B2

Reaction notes

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