3,5-Dimethylpiperidine → 2,7-bis(3,5-dimethylpiperidin-1-ylsulfonyl)-10-methylacridin-9(10H)-one

HRID 2271377Notes

Reaction equation

HRID 2271377 reaction equation
[CH3:1][N:2]1[C:15]2[C:10](=[CH:11][C:12]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:14]=2)[C:9](=[O:20])[C:8]2[CH:7]=[C:6]([S:21](Cl)(=[O:23])=[O:22])[CH:5]=[CH:4][C:3]1=2.[CH3:25][CH:26]1[CH2:31][CH:30]([CH3:32])[CH2:29][NH:28][CH2:27]1>C1COCC1>[CH3:25][CH:26]1[CH2:31][CH:30]([CH3:32])[CH2:29][N:28]([S:16]([C:12]2[CH:13]=[CH:14][C:15]3[N:2]([CH3:1])[C:3]4[C:8](=[CH:7][C:6]([S:21]([N:2]5[CH2:15][CH:10]([CH3:11])[CH2:9][CH:8]([CH3:7])[CH2:3]5)(=[O:23])=[O:22])=[CH:5][CH:4]=4)[C:9](=[O:20])[C:10]=3[CH:11]=2)(=[O:18])=[O:17])[CH2:27]1

Participants

4

Reactant 2

HCID 1182593,5-DimethylpiperidineHCID 59355212HCID 59355212, compound

Product 1

HCID 468511812,7-bis(3,5-dimethylpiperidin-1-ylsulfonyl)-10-methylacridin-9(10H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10-methyl-9-oxo-9,10-dihydroacridine-2,7-disulfonyl dichloride from Example 7 (810 mg, 2 mmole) in THF (20 mL) was added 3,5-dimethylpiperidine (2 mL, 15 mmole) and the reaction mixture was stirred at room temperature for 6 hours. Solvent was evaporated and the residue was treated with 1 N HCl (50 mL) and stirred for 10 minutes. Yellow product was collected by filtration, washed with water and methanol and dried. Crude material was crystallized from chloroform-ethanol to provide 900 mg (80%) of yellow 11-4. MS 560 (MH+).

Workup

  1. customSolvent was evaporated
  2. additionthe residue was treated with 1 N HCl (50 mL)
  3. stirringstirred for 10 minutes
  4. filtrationYellow product was collected by filtration
  5. washwashed with water and methanol
  6. customdried
  7. customCrude material was crystallized from chloroform-ethanol
  8. customto provide 900 mg (80%) of yellow 11-4

Sources & evidence

ORD record
ord-0ae59f7f6f4c4475ac094b14db351635
Source dataset
uspto-grants-2015_09
Patent number
US09120754B2

Reaction notes

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