1-Benzylpiperazine → HCID 68525626, compound

HRID 884188Notes

Reaction equation

HRID 884188 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1Cl)[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]2[CH:31]=[CH:30][C:18]([C:19]([N:21]3CCC(C(O)=O)[CH2:23][CH2:22]3)=[O:20])=[CH:17][CH:16]=2)=[N:12][CH:13]=1)=[O:6].[CH2:36](N1CCNCC1)[C:37]1C=CC=CC=1.[OH2:49].ON1[C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][C:54]=2N=N1.[ClH:60].[CH2:61]([N:63]=[C:64]=[N:65][CH2:66][CH2:67][CH2:68]N(C)C)[CH3:62].[C:72](=O)(O)[O-].[Na+]>CN(C=O)C>[CH2:72]([CH:68]1[CH2:67][CH2:66][N:65]([C:64]([N:63]2[CH2:61][CH2:62][N:21]([C:19]([C:18]3[CH:30]=[CH:31][C:15]([O:14][C:11]4[N:12]=[CH:13][C:8]([NH:7][C:5](=[O:6])[C:4]5[CH:32]=[CH:33][C:34]([Cl:60])=[C:2]([Cl:1])[CH:3]=5)=[CH:9][CH:10]=4)=[CH:16][CH:17]=3)=[O:20])[CH2:22][CH2:23]2)=[O:49])[CH2:37][CH2:36]1)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

7

Reactant 5

HCID 759941-BenzylpiperazineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68525974HCID 68525974, compound

Product 1

HCID 68525626HCID 68525626, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-{4-[5-(3,4-dichlorobenzoylamino)pyridin-2-yloxy]benzoyl}piperidine-4-carboxylic acid (4.5 g, 8.8 mmol) in DMF (88 mL) were added 1-benzylpiperazine (1.83 mL, 10.5 mmol), 1-hydroxybenzotriazole monohydrate (1.61 g, 10.5 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.02 g, 10.5 mmol) under ice cooling, and the resulting solution was stirred overnight at room temperature. To this reaction solution was added a saturated sodium bicarbonate solution, and the resulting solution was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was recrystallized from isopropyl alcohol (700 mL), to thereby yield 3.2 g of the title compound.

Workup

  1. extractionthe resulting solution was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was recrystallized from isopropyl alcohol (700 mL)

Sources & evidence

ORD record
ord-4d0bb6f5daad4db58b6181a839042da1
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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