Hydrochloric Acid → 2-[5-(4-Quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylic acid

HRID 1714784Notes

Reaction equation

HRID 1714784 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([NH:23][C:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=2[C:30]([O:32]CC)=[O:31])=[O:22])[CH2:13][CH2:12]1.[OH-].[Na+].Cl>CC(O)C.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([NH:23][C:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=2[C:30]([OH:32])=[O:31])=[O:22])[CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23155633Ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylate

Product 1

HCID 231556192-[5-(4-Quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylic acidYield 83.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

In 725 ml of 2-propanol and 365 ml of distilled water, 168.0 g of ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylate as synthesized in above Step 7-1-D was suspended. To the suspension 580 ml of 1N-aqueous sodium hydroxide was added and heated under reflux for 1.5 hours. After cooling, the reaction mixture was neutralized with 2N-hydrochloric acid. Whereupon precipitated crystals were recovered by filtration and dried to provide 131.8 g (83.4%) of 2-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylic acid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureAfter cooling
  4. customWhereupon precipitated crystals
  5. filtrationwere recovered by filtration
  6. customdried

Sources & evidence

ORD record
ord-939260406f504a74acfbd4acbf6b3f5f
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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