Ethanol → HCID 21993700, compound

HRID 1978377Notes

Reaction equation

HRID 1978377 reaction equation
C(O)=O.[C:4]([N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.BrC[CH2:20][CH2:21][CH2:22][C:23]1C=[CH:32][CH:31]=[C:25]2[C:26]([NH:28][C:29](=[O:30])[C:24]=12)=O.C(N(CC)CC)C.O.[CH2:42]([OH:44])[CH3:43]>>[C:4]([N:12]1[CH2:17][CH2:16][N:15]([CH2:32][CH2:31][CH2:25][CH2:26][N:28]2[C:42](=[O:44])[C:43]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:24]3[C:29]2=[O:30])[CH2:14][CH2:13]1)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 8471TriethylamineHCID 21960043BromobutylphthalimideHCID 70247550HCID 70247550, compound

Product 1

HCID 21993700HCID 21993700, compound

Procedure

A solution of 5.0 g (21.16 mmol.) of 1-benzoylpiperazine formate, 5.97 g (21.16 mmol.) of 4-bromobutylphthalimide and 9.0 ml (64.57 mmol.) of triethylamine in ethanol (50 ml) was heated for 40 hours under reflux. The reaction mixture was cooled to room temperature, to which was added water. The mixture was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous saline solution, which was then dried over magnesium sulfate, followed by distilling off the solvent under reduced pressure to leave a crude product. The crude product was purified by means of a column chromatography (methanol/ethyl acetate 5-10%). The solvent was distilled off under reduced pressure to give N-[4-(4-benzoylpiperazin-1-yl)butan-1-yl]phthalimide (6.99 g) as yellow oil. To a solution of 6.99 g of this compound in ethanol (50 ml) was added, at room temperature, 1.34 g (26.8 mmol.) of hydrazine monohydrate. The mixture was heated for 2 hours under reflux. The reaction mixture was cooled to room temperature. The resulting white solid substance was filtered off, and the filtrate was concentrated under reduced pressure. To the concentrate was added water, which was subjected to extraction with chloroform. The organic layer was washed with a saturated aqueous saline solution, which was dried over magnesium sulfate, followed by distilling off the solvent under reduced pressure to leave crude 4-(4-aminobutan-1-yl)-1-benzoylpiperazine. To an ethanol solution of this compound was added, at room temperature, 5 ml (60 mmol.) of 12N hydrochloric acid. The mixture was stirred for one hour at room temperature. The reaction mixture was concentrated under reduced pressure, to which was added diethyl ether. The resulting crystals were collected by filtration and washed with ethanol and diethyl ether to give the object compound as a white crystalline product. The yield was 2.92 g (41%).

Workup

  1. temperatureunder reflux
  2. extractionThe mixture was subjected to extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous saline solution, which
  4. dry with materialwas then dried over magnesium sulfate
  5. distillationby distilling off the solvent under reduced pressure
  6. customto leave a crude product
  7. customThe crude product was purified by means of a column chromatography (methanol/ethyl acetate 5-10%)
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a138d9b43e4245c888f5d3cecdcbe9ad
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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