1-Piperonylpiperazine → HCID 68528799, compound

HRID 884193Notes

Reaction equation

HRID 884193 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[Cl:35])[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]3[CH2:26][CH2:25][CH:24]([C:27](O)=[O:28])[CH2:23][CH2:22]3)=[O:20])=[CH:17][CH:16]=2)=[N:12][CH:13]=1)=[O:6].[CH2:36]([N:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1)[C:37]1[CH:45]=[CH:44][C:43]2[O:42][CH2:41][O:40][C:39]=2[CH:38]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C>[CH2:36]([N:46]1[CH2:51][CH2:50][N:49]([C:27]([CH:24]2[CH2:25][CH2:26][N:21]([C:19]([C:18]3[CH:17]=[CH:16][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:35])=[C:2]([Cl:1])[CH:3]=5)=[CH:9][CH:10]=4)=[CH:31][CH:30]=3)=[O:20])[CH2:22][CH2:23]2)=[O:28])[CH2:48][CH2:47]1)[C:37]1[CH:45]=[CH:44][C:43]2[O:42][CH2:41][O:40][C:39]=2[CH:38]=1

Participants

6

Reactant 4

HCID 944261-PiperonylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68525974HCID 68525974, compound

Product 1

HCID 68528799HCID 68528799, 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 (7.96 g, 15.5 mmol) in DMF (160 mL) were added 1-piperonylpiperazine (3.75 g, 17.6 mmol), 1-hydroxybenzotriazole monohydrate (2.85 g, 18.6 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.56 g, 18.6 mmol) under ice cooling, and the resulting solution was stirred for overnight at room temperature. This reaction solution was concentrated under reduced pressure. To the residue were added water and ethyl acetate, and the resulting solution was vigorously stirred. The resulting precipitates were collected by filtration and recrystallized from a dichloromethane-methanol mixed solvent, to thereby yield 7.36 g of the title compound.

Workup

  1. concentrationThis reaction solution was concentrated under reduced pressure
  2. additionTo the residue were added water and ethyl acetate
  3. stirringthe resulting solution was vigorously stirred
  4. customThe resulting precipitates
  5. filtrationwere collected by filtration
  6. customrecrystallized from a dichloromethane-methanol mixed solvent

Sources & evidence

ORD record
ord-7652e7b6bfd64d70943b3da4d60d7144
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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