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

HRID 582306Notes

Reaction equation

HRID 582306 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].C(N(CC)CC)C.Br[CH2:41][CH2:42][CH2:43][OH:44]>C(O)C>[OH:44][CH2:43][CH2:42][CH2:41][N:28]1[CH2:27][CH2:26][N:25]([C:23](=[O:24])[C:22]2[CH:21]=[CH:20][C:19]([C:17]([N:14]3[CH2:15][CH2:16][N:11]([C:6]4[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[CH:10][CH:9]=[CH:8][N:7]=4)[CH2:12][CH2:13]3)=[O:18])=[CH:32][CH:31]=2)[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123083-Bromo-1-propanolHCID 540321271-[4-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoyl]piperazine

Product 1

HCID 572740104-(3-Hydroxypropyl)-1-[4-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoyl]piperazineYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[4-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoyl]piperazine (0.5 g) was dissolved in anhydrous ethanol (25 ml) and then, triethylamine (0.3 ml) and 3-bromo-1-propanol (0.5 g) were added. The solution was heated to reflux for 12 hours. The solvent was concentrated under reduced pressure and then, the residue was dissolved in chloroform (50 ml), and the solution was washed with water twice. Water (40 ml), methanol (5 ml) and aqueous 10% sodium hydroxide (10 ml) were added to chloroform solution and the mixture was stirred for 1 hour. The separated organic layers were washed with water and the solvent was concentrated under reduced pressure. The concentrated residue was crystallized by treatment with ether, and further recrystallized using ethyl acetate and ether, filtered and dried to give 0.44 g (yield: 78%) of the desired compound as white crystal.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 12 hours
  3. concentrationThe solvent was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in chloroform (50 ml)
  5. washthe solution was washed with water twice
  6. additionWater (40 ml), methanol (5 ml) and aqueous 10% sodium hydroxide (10 ml) were added to chloroform solution
  7. washThe separated organic layers were washed with water
  8. concentrationthe solvent was concentrated under reduced pressure
  9. customThe concentrated residue was crystallized by treatment with ether
  10. customfurther recrystallized
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-44dfe2c8848440c1b6caafd07e37336b
Source dataset
uspto-grants-1999_07
Patent number
US05922871

Reaction notes

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