Toluene → 3-[4-[4-(2-Pyrimidinyl)-1-piperazinyl]butyl]-9-thia-3-azabicyclo[3.3.1]nonane-2,4-dione

HRID 1253260Notes

Reaction equation

HRID 1253260 reaction equation
[S:1]1[CH:6]2[C:7]([O:9][C:10](=[O:11])[CH:2]1[CH2:3][CH2:4][CH2:5]2)=O.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[N:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[CH2:19][CH2:18]1.C1(C)C=CC=CC=1>O>[N:24]1[CH:25]=[CH:26][CH:27]=[N:28][C:23]=1[N:20]1[CH2:21][CH2:22][N:17]([CH2:16][CH2:15][CH2:14][CH2:13][N:12]2[C:7](=[O:9])[CH:6]3[S:1][CH:2]([CH2:3][CH2:4][CH2:5]3)[C:10]2=[O:11])[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 128407054-(2-Pyrimidinyl)-1-piperazinebutanamineHCID 54010570Tetrahydrothiopyran-2,6-dicarboxylic anhydride

Product 1

HCID 141563613-[4-[4-(2-Pyrimidinyl)-1-piperazinyl]butyl]-9-thia-3-azabicyclo[3.3.1]nonane-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tetrahydrothiopyran-2,6-dicarboxylic anhydride (2.4 g., 14 mmole) and 1-(4-aminobutyl)-4-(2-pyrimidinyl)piperazine (3.5 g., 15 mmole) were dissolved in 250 ml. of toluene and refluxed for 48 hours with water removal via a Dean-Shark trap. The solvent was removed in vacuum and replaced with chloroform. The mixture was filtered through 75 g. of silica gel and concentrated in vacuum and the residue was crystallized from isopropanol with addition of 4N isopropanolic HCl. A second crystallization from isopropanol gave 1. g. of the title compound as the monohydrochloride; m.p. 238°-241° C. (d).

Workup

  1. customThe solvent was removed in vacuum
  2. filtrationThe mixture was filtered through 75 g
  3. concentrationof silica gel and concentrated in vacuum
  4. customthe residue was crystallized from isopropanol with addition of 4N isopropanolic HCl
  5. customA second crystallization from isopropanol
  6. customgave 1

Sources & evidence

ORD record
ord-770ee10cdb5d484bb927337d76abfdf5
Source dataset
uspto-grants-1988_05
Patent number
US04748240

Reaction notes

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