HCID 18770425, compound → HCID 15491073, compound

HRID 479404Notes

Reaction equation

HRID 479404 reaction equation
Cl.Cl.[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([C:52]2[CH:57]=[C:56]([O:58][CH3:59])[C:55]([O:60][CH3:61])=[C:54]([O:62][CH3:63])[CH:53]=2)=[C:10]([CH:51]=1)[C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][N:25]([C:28](=[O:50])[C:29]3[CH:34]=[C:33]([N+:35]([O-])=O)[CH:32]=[CH:31][C:30]=3[C:38]3[CH:43]=[C:42]([O:44][CH3:45])[C:41]([O:46][CH3:47])=[C:40]([O:48][CH3:49])[CH:39]=3)[CH2:24][CH2:23]2)[CH2:15][CH2:14]1)=[O:12])([O-])=O>[Pd].C(O)(=O)C.CO>[NH2:35][C:33]1[CH:32]=[CH:31][C:30]([C:38]2[CH:39]=[C:40]([O:48][CH3:49])[C:41]([O:46][CH3:47])=[C:42]([O:44][CH3:45])[CH:43]=2)=[C:29]([CH:34]=1)[C:28]([N:25]1[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][CH2:19][N:16]2[CH2:17][CH2:18][N:13]([C:11](=[O:12])[C:10]3[CH:51]=[C:6]([NH2:3])[CH:7]=[CH:8][C:9]=3[C:52]3[CH:53]=[C:54]([O:62][CH3:63])[C:55]([O:60][CH3:61])=[C:56]([O:58][CH3:59])[CH:57]=3)[CH2:14][CH2:15]2)[CH2:23][CH2:24]1)=[O:50]

Participants

4

Reactant 1

HCID 18770425HCID 18770425, compound

Product 1

HCID 15491073HCID 15491073, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

10% Palladium on carbon (50 mg) was added to a solution in acetic acid-methanol (1 ml—1 ml) of 1,3-bis[4-[5-nitro-2-(3,4,5-trimethoxyphenyl)benzoyl]1-piperazinyl]propane dihydrochloride (91 mg; 0.10 mmol) synthesized by the process described in Example 8. After the mixture was stirred at room temperature for 3 hours under hydrogen, the catalyst was removed from the reaction mixture by filtration. The filtrate was concentrated under reduced pressure, and a saturated aqueous solution of sodium hydrogencarbonate was added to the resultant concentrated residue to conduct extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel, thereby obtaining 29 mg (yield: 37%) of 1,3-bis[4-[5-amino-2-(3,4,5-trimethoxyphenyl)benzoyl]-1-piperazinyl]propane as a colorless oil.

Workup

  1. customsynthesized by the process
  2. customthe catalyst was removed from the reaction mixture by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additiona saturated aqueous solution of sodium hydrogencarbonate was added to the resultant concentrated residue
  5. extractionextraction with chloroform
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-98562e8de7094b6b8257c23d6ca73a82
Source dataset
uspto-grants-2003_11
Patent number
US06645957B2

Reaction notes

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