3,8-Dioxabicyclo[3.2.1]octane-2,4-dione → 3-[4-[4-(6-Chloro-2-pyrazinyl)-1-piperazinyl]butyl]-8-oxa-3-azabicyclo[3.2.1]octane-2,4-dione

HRID 1253265Notes

Reaction equation

HRID 1253265 reaction equation
[O:1]1[CH:5]2[C:6]([O:8][C:9](=[O:10])[CH:2]1[CH2:3][CH2:4]2)=O.[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[N:26][CH:25]=[C:24]([Cl:28])[N:23]=2)[CH2:18][CH2:17]1>C(Cl)Cl>[Cl:28][C:24]1[N:23]=[C:22]([N:19]2[CH2:18][CH2:17][N:16]([CH2:15][CH2:14][CH2:13][CH2:12][N:11]3[C:6](=[O:8])[CH:5]4[O:1][CH:2]([CH2:3][CH2:4]4)[C:9]3=[O:10])[CH2:21][CH2:20]2)[CH:27]=[N:26][CH:25]=1

Participants

4

Reactant 2

HCID 134257993,8-Dioxabicyclo[3.2.1]octane-2,4-dioneHCID 140865264-[4-(6-Chloropyrazin-2-yl)piperazin-1-yl]butan-1-amine

Product 1

HCID 141563713-[4-[4-(6-Chloro-2-pyrazinyl)-1-piperazinyl]butyl]-8-oxa-3-azabicyclo[3.2.1]octane-2,4-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tetrahydrofuran-2,5-dicarboxylic anhydride (1.26 g., 8.8 mmole) and 1-(4-aminobutyl)-4-(6-chloro-2-pyrazinyl)piperazine (2.37 g., 8.8 mmole) were combined and stirred for 30 minutes in 200 ml. of methylene chloride. The solvent was removed in vacuum and replaced with 300 ml. of xylene. The mixture as refluxed for 48 hours with water removal via a Dean-Stark trap. After cooling, the mixture was filtered through 75 g. of silica gel and the column rinsed with 5% ethanol/chloroform. The product was concentrated in vacuum and recrystallized from isopropanol with addition of 4N isopropanolic HCl. 0.60 Grams of the title compound was obtained as the monohydrochloride; m.p. 233°-235° C. (d).

Workup

  1. customThe solvent was removed in vacuum
  2. temperatureThe mixture as refluxed for 48 hours with water removal via a Dean-Stark trap
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through 75 g
  5. washof silica gel and the column rinsed with 5% ethanol/chloroform
  6. concentrationThe product was concentrated in vacuum
  7. customrecrystallized from isopropanol with addition of 4N isopropanolic HCl

Sources & evidence

ORD record
ord-9da688d532494728b3fdbb0b3f23bb24
Source dataset
uspto-grants-1988_05
Patent number
US04748240

Reaction notes

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