1,4-Dibromobutane → HCID 22010768, compound

HRID 323156Notes

Reaction equation

HRID 323156 reaction equation
CC1C=CC(C2C(C(N[C:17]3[CH:33]=[CH:32][CH:31]=[CH:30][C:18]=3[C:19]([N:21]([CH3:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[OH:28])=[O:20])=O)=CC=CC=2)=CC=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:41][CH2:42][CH2:43][CH2:44]Br.[CH3:46][C:47]1[CH:52]=[CH:51][C:50]([C:53]2[C:54]([C:59]([NH:61]C3C=CC=CC=3C(N(C)C3C=CC=CC=3OCCCCBr)=O)=[O:60])=[CH:55][CH:56]=[CH:57][CH:58]=2)=[CH:49][CH:48]=1.[CH3:84][N:85]1[CH2:90][CH2:89][NH:88][CH2:87][CH2:86]1>CN(C)C=O>[CH3:46][C:47]1[CH:48]=[CH:49][C:50]([C:53]2[C:54]([C:59]([NH:61][C:32]3[CH:31]=[CH:30][C:18]([C:19]([N:21]([CH3:29])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH2:41][CH2:42][CH2:43][CH2:44][N:88]4[CH2:89][CH2:90][N:85]([CH3:84])[CH2:86][CH2:87]4)=[O:20])=[CH:17][CH:33]=3)=[O:60])=[CH:55][CH:56]=[CH:57][CH:58]=2)=[CH:51][CH:52]=1

Participants

7

Reactant 5

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 22010724HCID 22010724, compoundHCID 22010867HCID 22010867, compound

Product 1

HCID 22010768HCID 22010768, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4′-methylbiphenyl-2-carboxamido-N-methyl-N-(2-hydroxyphenyl)benzamide (750 mg) in N,N-dimethylformamide (35 ml) was added potassium carbonate (1.42 g), 1,4-dibromobutane (1.11 g). The reaction mixture was stirred at 60° C. for 3 hours and to this mixture containing 4′-methylbiphenyl-2-carboxamido-N-methyl-N-[2-(4-bromobutoxy)phenyl]benzamide was added 1-methylpiperazine (1.03 g) and stirring was continued additional 15 hours. The mixture was extracted with ethyl acetate and washed with water and brine. The organic solution was dried over sodium sulfate. The solvent was removed by evaporation and purified by silica gel column chromatography (SiO2; 35 g, 5% methanol in dichloromethane) to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-[4-(4-methylpiperazin-1-yl)butoxy]phenyl]benzamide.

Workup

  1. stirringstirring
  2. waitwas continued additional 15 hours
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialThe organic solution was dried over sodium sulfate
  6. customThe solvent was removed by evaporation
  7. custompurified by silica gel column chromatography (SiO2; 35 g, 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-49623913b1914242b01f9e072e9da212
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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