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 494974Notes

Reaction equation

HRID 494974 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. Palladium carbon was removed by filtration, followed by concentration under a reduced pressure. The reaction solution was stirred under the same conditions for 10 hours 3 times, followed by concentration 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 following reaction without further purification.

Workup

  1. customPalladium carbon was removed by filtration
  2. concentrationfollowed by concentration under a reduced pressure
  3. concentrationfollowed by concentration 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-b442364b9bf04fdeb2a5a6cb67a719ed
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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