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4-Oxatricyclo[5.2.2.0,2,6]undecane-3,5-dione → N-[4-{4-(2-pyrimidinyl)-1-piperazinyl}-butyl]bicyclo[2.2.2]octane-2,3-dicarboximide hydrochloride

HRID 1719868
Notes
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Reaction equation

HRID 1719868 reaction equation
[CH:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]1[C:9]([O:11][C:12](=[O:13])[CH:2]21)=O.[NH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[N:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[CH2:21][CH2:20]1.[ClH:31].C(O)(C)C>N1C=CC=CC=1>[ClH:31].[N:26]1[CH:27]=[CH:28][CH:29]=[N:30][C:25]=1[N:22]1[CH2:23][CH2:24][N:19]([CH2:18][CH2:17][CH2:16][CH2:15][N:14]2[C:12](=[O:13])[CH:2]3[CH:3]([CH:4]4[CH2:5][CH2:6][CH:1]3[CH2:8][CH2:7]4)[C:9]2=[O:11])[CH2:20][CH2:21]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2522504-Oxatricyclo[5.2.2.0,2,6]undecane-3,5-dioneHCID 128407054-(2-Pyrimidinyl)-1-piperazinebutanamineHCID 21912024Isopropanol hydrochloride

Product 1

HCID 13422629N-[4-{4-(2-pyrimidinyl)-1-piperazinyl}-butyl]bicyclo[2.2.2]octane-2,3-dicarboximide hydrochloride

Reagents, catalysts & solvents 1

HCID 1049Pyridine
Solvent

Procedure

A mixture of bicyclo[2.2.2]octane-2,3-dicarboxylic anhydride (541 mg, 3 mmol), 1-(4-aminobutyl)-4-(2-pyrimidinyl)piperazine (708 mg, 3 mmol) and pyridine (12.1 ml) was refluxed for 10 hours. The solvent was removed from the mixture under reduced pressure. The residue was extracted with chloroform and water. The chloroform layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crude crystals (1 g), which were treated with 6% hydrogen chloride/isopropanol. The solvent was removed to give N-[4-{4-(2-pyrimidinyl)-1-piperazinyl}-butyl]bicyclo[2.2.2]octane-2,3-dicarboximide hydrochloride (from ethanol). M.P. 198°-200° C.

Workup

  1. temperaturewas refluxed for 10 hours
  2. customThe solvent was removed from the mixture under reduced pressure
  3. extractionThe residue was extracted with chloroform and water
  4. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give crude crystals (1 g), which
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-f40515e51ca340ef9a33043b42030872
Source dataset
uspto-grants-1985_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04543355

Reaction notes

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