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

HRID 551792Notes

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

Participants

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

customThe ethanol is evaporated under reduced pressure
additiona 1N aqueous hydrochloric acid solution is subsequently added
filtrationThe precipitate is filtered off
washwashed with water
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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