Hydrochloric Acid → 2-{3-[4-(4-bromo-2-methoxyphenyl)piperazin-1-yl]propylamino}-N,N-dimethylnicotinamide

HRID 2294154Notes

Reaction equation

HRID 2294154 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19]2[N:29]=[CH:28][CH:27]=[CH:26][C:20]=2[C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[CH2:11][CH2:10]1.Cl.[Br:31]N1C(=O)CCC1=O>C(Cl)Cl.CO.O.C([O-])([O-])=O.[K+].[K+]>[Br:31][C:7]1[CH:6]=[CH:5][C:4]([N:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19]3[N:29]=[CH:28][CH:27]=[CH:26][C:20]=3[C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[CH2:13][CH2:14]2)=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 67184N-bromobutanimideHCID 98655772-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propylamino)-N,N-dimethylnicotinamide

Product 1

HCID 214734832-{3-[4-(4-bromo-2-methoxyphenyl)piperazin-1-yl]propylamino}-N,N-dimethylnicotinamideYield 75.5%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 11430Potassium CarbonateSolvent

Procedure

2-{3-[4-(2-Methoxyphenyl)piperazin-1-yl]propylamino}-N,N-dimethylnicotinamide (0.21 g, 0.53 mmol), prepared as in Example 21, was dissolved in methylene chloride and the solution was treated with excess hydrochloric acid in methanol and concentrated under reduced pressure. The residue was dissolved in 6 mL of DMF and N-bromosuccinimide (0.101 g, 0.57 mmol) was added. The mixture was stirred at room temperature for approximately 24 hours, diluted with water and basified with K2CO3. The basified mixture was extracted with ethyl acetate and the ethyl acetate layer was washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified on silica gel by column chromatography eluting with 5% methanol/methylene chloride to give 2-{3-[4-(4-bromo-2-methoxyphenyl)piperazin-1-yl]propylamino}-N,N-dimethylnicotinamide (0.19 g, 0.40 mmol) as an oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 6 mL of DMF
  3. extractionThe basified mixture was extracted with ethyl acetate
  4. washthe ethyl acetate layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel by column chromatography
  9. washeluting with 5% methanol/methylene chloride

Sources & evidence

ORD record
ord-d495feaf3efc471bb2cd5223249bbbe7
Source dataset
uspto-grants-1997_11
Patent number
US05688795

Reaction notes

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