m-Chloroperbenzoic acid → HCID 373774, compound

HRID 1086618Notes

Reaction equation

HRID 1086618 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([C:16]1[C:17]2[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=2[N:23]=[C:24]2[C:29]=1[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:13][CH2:14][CH3:15]>C(Cl)Cl>[CH2:12]([C:16]1[C:17]2[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=2[N+:23]([O-:6])=[C:24]2[C:29]=1[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10890121Acridine, 9-butyl-1,2,3,4,5,6,7,8-octahydro-

Product 1

HCID 373774HCID 373774, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a 1 L round-bottomed flask equipped with a magnetic stirrer, a reflux condenser and a 250 ml addition funnel are placed 56.3 g (0.26 mol) of m-chloroperoxybenzoic acid (Note 12) and 350 mL of methylene chloride. The resulting suspension is stirred as a solution of 38.0 g (0.16 mol) of 9-n-butyl-1,2,3,4,5,6,7,8-octahydroacridine in 120 mL of methylene chloride is added rapidly. When the reaction mixture ceases to boil gently from the heat of reaction, the reaction flask is warmed to extend the reflux period to a total of 2.5 hrs. (Note 10). The reaction mixture is cooled to room temperature, extracted with 0.5 M aqueous sodium hydroxide (4× 450 mL), dried using anhydrous sodium sulfate and concentrated under reduced pressure using a rotary evaporator. Residual solvent is removed at 0.1 mm, yielding 40 g (99%) of 9-n-butyl-1,2,3,4,5,6,7,8-octahydroacridine-N-oxide as a yellow crystalline solid, mp 96-100° C.

Workup

  1. customInto a 1 L round-bottomed flask equipped with a magnetic stirrer, a reflux condenser and a 250 ml addition funnel
  2. additionis added rapidly
  3. temperatureheat of reaction
  4. temperaturethe reaction flask is warmed
  5. customto a total of 2.5 hrs
  6. extractionextracted with 0.5 M aqueous sodium hydroxide (4× 450 mL)
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customa rotary evaporator
  10. customResidual solvent is removed at 0.1 mm

Sources & evidence

ORD record
ord-89e79231816d4958b2ee28a60a71735c
Source dataset
uspto-grants-1991_07
Patent number
US05030728

Reaction notes

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