Diethyl Ether → HCID 22468602, compound

HRID 394975Notes

Reaction equation

HRID 394975 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][CH2:13][CH2:14][C:15]1([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]1)=[CH:9][C:8]([O:33][CH3:34])=[CH:7][CH:6]=2.C(OCC)C>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][CH2:13][CH2:14][C:15]1([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)=[CH:9][C:8]([O:33][CH3:34])=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 66688932Ethyl 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate

Product 1

HCID 22468602HCID 22468602, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
20 °C

Procedure

A mixture of 2.6 g of ethyl 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)-piperidine-4-carboxylate in 40 cm3 of dioxane, to which was added 14 cm3 of 4 N hydrochloric dioxane, was stirred for 16 hours at a temperature in the region of 20° C. The suspension obtained was diluted by addition of 100 cm3 of diethyl ether, stirred at about 20° C. for 1 hour and then filtered. The cake was washed with twice 40 cm3 of diethyl ether and then dried in a desiccator under reduced pressure (5 kPa). 1.9 g of ethyl 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate were obtained in the form of a white solid.

Workup

  1. customThe suspension obtained
  2. stirringstirred at about 20° C. for 1 hour
  3. filtrationfiltered
  4. washThe cake was washed with twice 40 cm3 of diethyl ether
  5. customdried in a desiccator under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-f193c79a36444653bb617528db43f087
Source dataset
uspto-grants-2003_08
Patent number
US06603005B2

Reaction notes

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