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Sodium Hydroxide → 1-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)piperidine-4-carboxylic acid

HRID 551792
Notes
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Reaction equation

HRID 551792 reaction equation
[N:1]1([C:11]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]([O:21]CC)=[O:20])[CH2:15][CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[N:1]1([C:11]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]([OH:21])=[O:20])[CH2:15][CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67188549ethyl 1-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)piperidine-4-carboxylate

Product 1

HCID 285131921-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)piperidine-4-carboxylic acidYield 93.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

11.2 g of ethyl 1-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)piperidine-4-carboxylate, 443 ml of ethanol and 163 ml of 1N aqueous sodium hydroxide solution are introduced into a 1 l round-bottomed flask. The reaction medium is heated at 50° C. for 4 h 30. The ethanol is evaporated under reduced pressure and a 1N aqueous hydrochloric acid solution is subsequently added. The precipitate is filtered off, washed with water and then dried under reduced pressure. 9.5 g of 1-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)piperidine-4-carboxylic acid are obtained.

Workup

  1. customThe ethanol is evaporated under reduced pressure
  2. additiona 1N aqueous hydrochloric acid solution is subsequently added
  3. filtrationThe precipitate is filtered off
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-415186ece2ee46fc916e7ad37b84259f
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07947834B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes