1-Phenylpiperazine → HCID 19003519, compound

HRID 2259406Notes

Reaction equation

HRID 2259406 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:10][CH2:11][CH2:12]Cl)[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH:22]1[CH:23]=[CH:24][C:25]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:26][CH:27]=1>CN(C=O)C>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:10][CH2:11][CH2:12][N:31]3[CH2:32][CH2:33][N:28]([C:25]4[CH:26]=[CH:27][CH:22]=[CH:23][CH:24]=4)[CH2:29][CH2:30]3)[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 190035086-Chloro-3-(3-chloropropyl)-2(3H)-benzothiazolone

Product 1

HCID 19003519HCID 19003519, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of compound (X) (3.71 g, 20 mmol), K2CO3 (3.31 g, 24 tool), phenylpiperazine (XIb) (3.24 g, 20 mmol), and KI (3.98 g, 24 mmol) in DMF (20 ml) was stirred at 100° C. for 5 hours and concentrated in vacuo. The residue was extracted with dichloromethane, washed with a saturated saline solution and dried over MgSO4. The dichloromethane layer was subjected to column chromatography on silica gel. The eluate eluted with dichloromethane/ethyl acetate (4/1) was recrystallized from ethyl ether to obtain compound (XIIb) (4.8 g, yield=61.9%) as colorless prism-shaped crystals.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe residue was extracted with dichloromethane
  3. washwashed with a saturated saline solution
  4. dry with materialdried over MgSO4
  5. washThe eluate eluted with dichloromethane/ethyl acetate (4/1)
  6. customwas recrystallized from ethyl ether
  7. customto obtain compound (XIIb) (4.8 g, yield=61.9%) as colorless prism-shaped crystals

Sources & evidence

ORD record
ord-b17b4fc29a584e418816b2000e236a1d
Source dataset
uspto-grants-1995_12
Patent number
US05473066

Reaction notes

Loading…