4-Methylmorpholine → 4-Cyclopentyl-1-[4-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoyl]piperazine

HRID 582304Notes

Reaction equation

HRID 582304 reaction equation
[CH:1]([NH:4][C:5]1[C:6]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:32]=[CH:31][C:22]([C:23]([N:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[O:24])=[CH:21][CH:20]=3)=[O:18])[CH2:13][CH2:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].CN1CCOCC1.[CH:40]1(Br)[CH2:44][CH2:43][CH2:42][CH2:41]1>C(#N)C>[CH:40]1([N:28]2[CH2:27][CH2:26][N:25]([C:23](=[O:24])[C:22]3[CH:21]=[CH:20][C:19]([C:17]([N:14]4[CH2:15][CH2:16][N:11]([C:6]5[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[CH:10][CH:9]=[CH:8][N:7]=5)[CH2:12][CH2:13]4)=[O:18])=[CH:32][CH:31]=3)[CH2:30][CH2:29]2)[CH2:44][CH2:43][CH2:42][CH2:41]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 8728BromocyclopentaneHCID 540321271-[4-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoyl]piperazine

Product 1

HCID 539943164-Cyclopentyl-1-[4-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoyl]piperazineYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-[4-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoyl]piperazine (0.5 g) was dissolved in acetonitrile (25 ml) and then, N-methylmorpholine (0.17 ml) and cyclopentyl bromide (0.3 ml) were added. The solution was heated to 65~75° C. and stirred for 20 hours. The solvent was concentrated under reduced pressure and then, the residue was dissolved in chloroform (40 ml). The solution was washed with water twice and the solvent was concentrated under reduced pressure. The concentrated residue was crystallized by treatment with ether and hexane, and further recrystallized using ethanol and isopropyl ether. The recrystallized product was filtered and dried to give 0.41 g (yield: 71%) of the desired compound.

Workup

  1. temperatureThe solution was heated to 65~75° C.
  2. concentrationThe solvent was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform (40 ml)
  4. washThe solution was washed with water twice
  5. concentrationthe solvent was concentrated under reduced pressure
  6. customThe concentrated residue was crystallized by treatment with ether and hexane
  7. customfurther recrystallized
  8. filtrationThe recrystallized product was filtered
  9. customdried

Sources & evidence

ORD record
ord-a3597ae2db534231925a08ec2beb3f2e
Source dataset
uspto-grants-1999_07
Patent number
US05922871

Reaction notes

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