1,3-Dibromopropane → HCID 14364333, compound

HRID 1278615Notes

Reaction equation

HRID 1278615 reaction equation
C(N1CCN([CH2:14][CH2:15][CH2:16][N:17]2[CH:21]([CH3:22])[CH2:20][CH2:19][C:18]2=[O:23])CC1)C1C=CC=CC=1.CC1NC(=O)CC1.[H-].[Na+].[Br:33]CCCBr>O1CCCC1.O>[Br:33][CH2:14][CH2:15][CH2:16][N:17]1[CH:21]([CH3:22])[CH2:20][CH2:19][C:18]1=[O:23].[CH2:16]([N:17]1[CH:21]([CH3:22])[CH2:20][CH2:19][C:18]1=[O:23])[CH:15]=[CH2:14]

Participants

8

Reactant 4

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 660555-Methyl-2-pyrrolidoneHCID 18430921HCID 18430921, compound

Product 2

HCID 14364333HCID 14364333, compoundHCID 70151694HCID 70151694, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

1-[3-(4-Benzyl-1-piperazinyl)propyl]-5-methyl-2-pyrrolidinone A solution of 5-methyl-2-pyrrolidinone (0.99 g/10.0 mmol) in tetrahydrofuran (10 ml) was added to a suspension of sodium hydride(60% in oil, 0.6 g/1 5.0 mmol) in tetrahydrofuran (50 ml) at 0° C. and the resulting mixture was stirred for 1 hour at ambient temperature. To the mixture was added a solution of 1,3-dibromopropane (5.1 ml/50.0 mmol) in tetrahydrofuran (10 ml) and the mixture was stirred for 1 day. The mixture was poured into water (50 ml) and extracted with ethyl acetate (50 ml×2). The combined extracts were washed with brine (50 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (Si, 230-400 mesh/dichloromethane:methanol=30:1) to give as a mixture of 1-(3-bromoproyl)-5-methyl-2-pyrrolidinone and 1-allyl-5-methyl-2-pyrrolidinone (0.8 g). The mixture was dissolved with ethanol (5 ml). To the solution was added 1-benzylpiperazine (0.4 mV/2.19 mmol), and the mixture was stand for 7 days. The solvent was removed in vacuo. The residue was dissolved in dichloromethane (20 ml) and 2N-NaOH (20 ml). The aqueous layer was extracted with dichloromethane (20 ml). The combined extracts were washed with brine (20 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (Si, 230-400 mesh/dichloromethane:methanol=30:1-15:1) to give as the titled compound (0.59 g/19%).

Workup

  1. stirringthe mixture was stirred for 1 day
  2. extractionextracted with ethyl acetate (50 ml×2)
  3. washThe combined extracts were washed with brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (Si, 230-400 mesh/dichloromethane:methanol=30:1)

Sources & evidence

ORD record
ord-45064d72acd546e9b8854ea56eb66411
Source dataset
uspto-grants-2002_09
Patent number
US06444677B2

Reaction notes

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