Sodium Hydroxide → HCID 12902718, compound

HRID 1388800Notes

Reaction equation

HRID 1388800 reaction equation
C1C=C(C(O)=[O:8])C(C(OO)=O)=CC=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]=[CH:21][CH:20]=[C:19]2[CH2:26][CH2:27][CH:28]1[CH2:33][CH2:32][N:31]([C:34](=[O:41])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:30][CH2:29]1.[OH-].[Na+]>CCOCC.CO>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N+:22]([O-:8])=[CH:21][CH:20]=[C:19]2[CH2:26][CH2:27][CH:28]1[CH2:29][CH2:30][N:31]([C:34](=[O:41])[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:32][CH2:33]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 75329Monoperoxyphthalic acid2×HCID 12902717HCID 12902717, compound

Product 1

HCID 12902718HCID 12902718, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
10 °C

Procedure

269 ml of a 0.09 M solution of monoperphthalic acid in ether (prepared according VOGEL-Textbook of Practical Organic Chemistry, 1978,307) are added rapidly to a solution of 7.9 g of 6-methoxy-4-[2-(1-benzoyl-4-piperidyl)-ethyl]-quinoline in 45 ml of methanol, stirred and cooled to 10° C. After four hours at the ambient temperature, a further 20 ml of the same monoperphthalic acid solution are added, and the stirring is then maintained for 15 hours. The reaction mixture is then made alkaline with 100 ml of a 0.7 N aqueous solution of sodium hydroxide. The organic phase, separated, is again washed with 100 ml of a 0.5 N solution of sodium hydroxide, dried, then concentrated. The residue obtained, after recrystallization from cyclohexane, gives 5.1 g of 6-methoxy-4-[2-(1-benzoyl-4-piperidyl)-ethyl]quinoline-N-oxide melting at 138° C.

Workup

  1. temperaturethe stirring is then maintained for 15 hours
  2. customThe organic phase, separated
  3. washis again washed with 100 ml of a 0.5 N solution of sodium hydroxide
  4. customdried
  5. concentrationconcentrated
  6. customThe residue obtained
  7. customafter recrystallization from cyclohexane

Sources & evidence

ORD record
ord-35fb1559d7ef41a0ae045b22343b03a0
Source dataset
uspto-grants-1984_02
Patent number
US04433150

Reaction notes

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