7-(2-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-methoxyquinoline → 7-(2-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-methoxy-1,2,3,4-tetrahydroquinoline

HRID 494970Notes

Reaction equation

HRID 494970 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([CH2:11][CH2:12][C:13]3[CH:22]=[C:21]4[C:16]([CH:17]=[CH:18][CH:19]=[N:20]4)=[CH:15][C:14]=3[O:23][CH3:24])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H][H]>CO.[C].[Pd]>[O:4]1[C:5]2([CH2:6][CH2:7][N:8]([CH2:11][CH2:12][C:13]3[CH:22]=[C:21]4[C:16]([CH2:17][CH2:18][CH2:19][NH:20]4)=[CH:15][C:14]=3[O:23][CH3:24])[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 576827747-(2-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-methoxyquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 576829147-(2-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-methoxy-1,2,3,4-tetrahydroquinolineYield 101.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

445 mg of 7-(2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-methoxyquinoline was dissolved in 10 ml of methanol. Thereafter, 100 mg of 10% palladium carbon was added to the reaction solution. The obtained mixture was stirred for 6 hours under a 4 kg/cm2 of hydrogen atmosphere. Thereafter, palladium carbon was removed by filtration, and the filtrate was concentrated under a reduced pressure. The reaction solution was stirred under the same above conditions for 10 hours 3 times, and then, it was concentrated under a reduced pressure. A saturated sodium bicarbonate aqueous solution was added to the residue, followed by extraction with chloroform. The extract was dried over magnesium sulfate and then concentrated under a reduced pressure, so as to obtain 459 mg of 7-(2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-methoxy-1,2,3,4-tetrahydroquinoline. This compound was used in the next reaction without further purification.

Workup

  1. customThereafter, palladium carbon was removed by filtration
  2. concentrationthe filtrate was concentrated under a reduced pressure
  3. concentrationit was concentrated under a reduced pressure
  4. additionA saturated sodium bicarbonate aqueous solution was added to the residue
  5. extractionfollowed by extraction with chloroform
  6. dry with materialThe extract was dried over magnesium sulfate
  7. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-31d7973449d848699dceeafba0ed7c6a
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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