1-Phenylpiperazine → HCID 9874288, compound

HRID 987592Notes

Reaction equation

HRID 987592 reaction equation
Cl[C:2]1[C:3]([S:25]([N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)(=[O:27])=[O:26])=[CH:4][C:5]([S:16]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)(=[O:18])=[O:17])=[C:6]([N:8]([CH2:14][CH3:15])[CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])[CH:7]=1.[C:34]1([N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH2:14]([N:8]([C:6]1[CH:7]=[C:2]([N:43]2[CH2:44][CH2:45][N:40]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:41][CH2:42]2)[C:3]([S:25]([N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)(=[O:26])=[O:27])=[CH:4][C:5]=1[S:16]([N:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1)(=[O:18])=[O:17])[CH2:9][CH2:10][N:11]([CH3:12])[CH3:13])[CH3:15]

Participants

3

Reactant 2

HCID 70961-PhenylpiperazineHCID 22986983HCID 22986983, compound

Product 1

HCID 9874288HCID 9874288, compound

Conditions

Temperature
90 °C

Procedure

2.63 g (5.1 mmol) of N-[5-chloro-2,4-bis-(piperidine-1-sulfonyl)-phenyl]-N-ethyl-N′,N′-dimethylethane-1,2-diamine, prepared as described below, are dissolved in 12 ml of 4-phenylpiperazine, and the reaction mixture is stirred at 90° C. for 9 hours. Workup entails extraction with ethyl acetate/water, drying of the combined organic phases over sodium sulfate, and removing the extractant under reduced pressure in a rotary evaporator. This is followed by purification by chromatography on silica gel (40-63μ, Merck Darmstadt; mobile phase=dichloromethane/methanol=20/1).

Workup

  1. extractionextraction with ethyl acetate/water
  2. dry with materialdrying of the combined organic phases over sodium sulfate
  3. customremoving the extractant under reduced pressure
  4. customin a rotary evaporator
  5. customThis is followed by purification by chromatography on silica gel (40-63μ, Merck Darmstadt; mobile phase=dichloromethane/methanol=20/1)

Sources & evidence

ORD record
ord-41554ae64c8f4a6782f4de650ae288fc
Source dataset
uspto-grants-2003_10
Patent number
US06632838B1

Reaction notes

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