Sodium Hydroxide → HCID 12902718, compound

HRID 2164602Notes

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

Conditions

Temperature: 10 °C

Procedure

269 ml of a 0.09M 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 0.7N aqueous solution of sodium hydroxide. The organic phase, separated, is again washed with 100 ml of a 0.5N 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

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

Sources & evidence

ORD record: ord-5084a42e29c444c985bd74991d0eeea8
Source dataset: uspto-grants-1985_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04505916

Reaction notes

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