Formate → HCID 13646236, compound

HRID 1978378Notes

Reaction equation

HRID 1978378 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15]([O-:17])=O.BrCCC[C:22]1[CH:32]=[CH:31][CH:30]=[C:24]2[C:25]([NH:27][C:28](=O)[C:23]=12)=[O:26].[CH2:33](N(CC)CC)[CH3:34]>C(O)C.O>[C:1]([N:9]1[CH2:14][CH2:13][N:12]([CH2:33][CH2:34][CH2:28][N:27]2[C:25](=[O:26])[C:24]3=[CH:23][CH:22]=[CH:32][CH:31]=[C:30]3[C:15]2=[O:17])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 283FormateHCID 8471TriethylamineHCID 7626541-BenzoylpiperazineHCID 21958088Bromopropylphthalimide

Product 1

HCID 13646236HCID 13646236, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 5.0 g (21.16 mmol.) of 1-benzoylpiperazine.formate, 5.67 g (21.15 mmol.) of 3-bromopropylphthalimide and 9.0 ml (64.57 mmol.) of triethylamine in ethanol (50 ml) was heated under reflux for 18 hours under nitrogen atmosphere. 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 dried over magnesium sulfate, followed by distilling off the solvent under reduced pressure. The resulting crude product was purified by means of a column chromatography (methanol/ethyl acetate 5%), followed by distilling off the solvent under reduced pressure, to give N-[3-(4-benzoylpiperazin-1-yl)propan-1-yl]phthalimide (6.22 g) as yellow oil. To an ethanol (50 ml) solution of this compound (6.22 g) was added, at room temperature, 1.24 g (24.8 mmol.) of hydrazine monohydrate. The mixture was heated for 2 hours under reflux. The reaction mixture was cooled to room temperature, then the resulting white solid substance was filtered off. 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, followed by drying over magnesium sulfate. the solvent was distilled off under reduced pressure to leave crude 4-(3-aminopropan-1-yl)-1-benzoylpiperazine. To an ethanol solution of this crude 4-(3-aminopropan-1-yl)-1-benzoylpiperazine was added, at room temperature, 3 ml (36 mmol.) of 12N hydrochloric acid. The mixture was stirred for one hour at room temperature. The reaction mixture was concentrated under reduced pressure. To the concentrate 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 1.80 g (27%).

Workup

  1. temperatureunder reflux for 18 hours under nitrogen atmosphere
  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 dried over magnesium sulfate
  5. distillationby distilling off the solvent under reduced pressure
  6. customThe resulting crude product was purified by means of a column chromatography (methanol/ethyl acetate 5%)
  7. distillationby distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-83e42a0d2d664266ab85d882baabdf16
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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