N-Piperidinoethanol → HCID 131712295, compound

HRID 1277976Notes

Reaction equation

[CH:1]1[N:5]2[C:6]3[C:11]([CH:12]=[CH:13][C:4]2=[N:3][C:2]=1[C:14]([OH:16])=[O:15])=[CH:10][CH:9]=[CH:8][CH:7]=3.C(C1NC=CN=1)(C1NC=CN=1)=O.[OH:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>CN(C=O)C>[OH2:15].[CH:1]1[N:5]2[C:6]3[C:11]([CH:12]=[CH:13][C:4]2=[N:3][C:2]=1[C:14]([O:16][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:15])=[CH:10][CH:9]=[CH:8][CH:7]=3.[N:32]1([CH2:31][CH2:30][O:29][C:14]([C:2]2[N:3]=[C:4]3[CH:13]=[CH:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]3[CH:1]=2)=[O:15])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

Conditions

Temperature: 80 °C

Procedure

0.85 g of imidazo-[1,2-a]-quinoline-2-carboxylic acid was dissolved in 25 ml of dry DMF and then 0.72 g of carbonyl diimidazole was added with stirring. The temperature was raised to 80° C. for 15 minutes and 0.57 g of (2-hydroxyethyl) piperidine was then added. The mixture was stirred at 100° C. for 3 hours and was cooled to room temperature and filtered. Then, 50 ml of water were added dropwise to the filtrate and the precipitate was filtered off, washed with water and dried under vacuum. This solid was crystallized from ethyl acetate/petroleum ether to obtain 2-piperidinoethyl imidazo-[1,2-a]-quinoline-2-carboxylate hemihydrate melting at 147°-150° C.

Workup

stirringThe mixture was stirred at 100° C. for 3 hours
temperaturewas cooled to room temperature
filtrationfiltered
additionThen, 50 ml of water were added dropwise to the filtrate
filtrationthe precipitate was filtered off
washwashed with water
customdried under vacuum
customThis solid was crystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record: ord-b229334999c74c048f4af179f0af2a69
Source dataset: uspto-grants-1981_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04279912

Reaction notes

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