O-Xylene → 3-[4-[4-(2-Quinolyl)-1-piperazinyl]butyl]-3-azabicyclo[3.2.1]octane-2,4-dione

HRID 1253262Notes

Reaction equation

HRID 1253262 reaction equation
[CH:1]1([C:9]([OH:11])=O)[CH2:5][CH2:4][CH:3]([C:6]([OH:8])=O)[CH2:2]1.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=2)[CH2:19][CH2:18]1.C1(C)C(C)=CC=CC=1>O>[N:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:31]=[CH:32][C:23]=1[N:20]1[CH2:19][CH2:18][N:17]([CH2:16][CH2:15][CH2:14][CH2:13][N:12]2[C:6](=[O:8])[CH:3]3[CH2:2][CH:1]([CH2:5][CH2:4]3)[C:9]2=[O:11])[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 1072161,3-Cyclopentanedicarboxylic acidHCID 212437031-(4-Aminobutyl)-4-(2-quinolyl)piperazine

Product 1

HCID 141563653-[4-[4-(2-Quinolyl)-1-piperazinyl]butyl]-3-azabicyclo[3.2.1]octane-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,3-Cyclopentane dicarboxylic acid (1.6 g., 10 mmole) and 1-(4-aminobutyl)-4-(2-quinolyl)piperazine (2.8 g., 10 mmole) were combined in 200 ml. of xylene and refluxed for 24 hours with water removal via a Dean-Stark trap. The solvent was then removed in vacuum and the residue redissolved in chloroform and filtered through 75 g. of silica gel. The column was rinsed with 5% ethanol/chloroform and the product-containing fractions were combined and evaporated. The residue was recrystallized from isopropanol with the addition of 4N isopropanolic HCl to give 820 mg. of the title compound as the dihydrochloride hemihydrate; m.p. 240°-242° C.

Workup

  1. customThe solvent was then removed in vacuum
  2. dissolutionthe residue redissolved in chloroform
  3. filtrationfiltered through 75 g
  4. washThe column was rinsed with 5% ethanol/chloroform
  5. customevaporated
  6. customThe residue was recrystallized from isopropanol with the addition of 4N isopropanolic HCl
  7. customto give 820 mg

Sources & evidence

ORD record
ord-b085f95e938f4d4f9b60dc63473ae7dd
Source dataset
uspto-grants-1988_05
Patent number
US04748240

Reaction notes

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