Reaction #2358561

ord-7077068609914dd5a271d8b8b3964d52

Reaction equation

CC1CC(C)CN(S(=O)(=O)c2ccc3c(c2)c(=S)c2cc(S(=O)(=O)N4CC(C)CC(C)C4)ccc2n3C)C1
2,7-bis(3,5-dimethylpiperidin-1-ylsulfonyl)-10-methylacridine-9(10H)-thione
Cl.NO
hydroxylamine hydrochloride
→
CC1CC(C)CN(S(=O)(=O)c2ccc3c(c2)c(=NO)c2cc(S(=O)(=O)N4CC(C)CC(C)C4)ccc2n3C)C1
title compound
Yield 85.3%
CC1CC(C)CN(S(=O)(=O)c2ccc3c(c2)c(=NO)c2cc(S(=O)(=O)N4CC(C)CC(C)C4)ccc2n3C)C1
2,7-bis(3,5-dimethylpiperidin-1-ylsulfonyl)-9-hydroxyimino-10-methyl-(9H,10H)-acridine
Yield 85.3%

Reactants

CC1CC(C)CN(S(=O)(=O)c2ccc3c(c2)c(=S)c2cc(S(=O)(=O)N4CC(C)CC(C)C4)ccc2n3C)C1
2,7-bis(3,5-dimethylpiperidin-1-ylsulfonyl)-10-methylacridine-9(10H)-thione
Cl.NO
hydroxylamine hydrochloride

Reagents

None

Solvents

c1ccncc1
pyridine

Conditions

Temperature
100°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherSolvent was removed
  2. 2
    workup.ADDITIONthe residue was treated with water
  3. 3
    Otherto remove excess of hydroxylamine
  4. 4
    OtherCrude material was crystallized from methanol-water

Procedure

To a solution of 2,7-bis(3,5-dimethylpiperidin-1-ylsulfonyl)-10-methylacridine-9(10H)-thione (290 mg, 0.5 mmole) in pyridine (5 mL) was added hydroxylamine hydrochloride (210 mg, 30 mmole) and the mixture was stirred at 100° C. for 8 hrs. Solvent was removed and the residue was treated with water to remove excess of hydroxylamine. Crude material was crystallized from methanol-water to give 245 mg (85%) of the title compound. MS 575 (MH+).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09120754B2uspto-grants-2015_09