Hydrochloric Acid → 8-(4-methylpiperazin-1-yl)-4H-quinolizin-4-one-3-carboxylic acid hydrochloride

HRID 1450073Notes

Reaction equation

F[C:2]1[C:11]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:10][C:9]2[N:4]([C:5](=[O:26])[C:6]([C:21]([O:23]CC)=[O:22])=[CH:7][C:8]=2NC)[CH:3]=1.[OH-].[Na+].[ClH:29]>C1COCC1>[ClH:29].[CH3:18][N:15]1[CH2:16][CH2:17][N:12]([C:11]2[CH:2]=[CH:3][N:4]3[C:9]([CH:10]=2)=[CH:8][CH:7]=[C:6]([C:21]([OH:23])=[O:22])[C:5]3=[O:26])[CH2:13][CH2:14]1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 1 g (2.75 mmol)of ethyl 7-fluoro-1-methylamino-8-(4-methylpiperazin-1-yl)-4H-quinolizin-4-one-3-carboxylate, from Step 7, in 12 mL of THF and 16.5 mL of a 0.5N aqueous solution of sodium hydroxide is heated, with stirring, at 75° C. for 8 hours. The THF is removed from the reaction mixture by distillation during the reaction. The concentrated reaction mixture is cooled to ambient temperature and adjusted to pH 2.0 with 10.5 mL of 1N aqueous hydrochloric acid solution. The aqueous solution is concentrated in vacuo to remove ~80% of the water and the concentrate is diluted with 50 mL of 95% ethyl alcohol. The solid is collected by filtration, washed with 2×5 mL of ethyl alcohol and dried in vacuo to afford the desired product.

Workup

customThe THF is removed from the reaction mixture by distillation during the reaction
customThe concentrated reaction mixture
temperatureis cooled to ambient temperature
concentrationThe aqueous solution is concentrated in vacuo
customto remove ~80% of the water
additionthe concentrate is diluted with 50 mL of 95% ethyl alcohol
filtrationThe solid is collected by filtration
washwashed with 2×5 mL of ethyl alcohol
customdried in vacuo

Sources & evidence

ORD record: ord-af1e09ca0b6c4bafb5f3b5ac5c3262a9
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05599816

Reaction notes

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