HCID 67539481, compound → 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-3,4-dihydroquinolin-2(1H)-one hydrochloride

HRID 40010Notes

Reaction equation

HRID 40010 reaction equation
[ClH:1].[O:2]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][NH:13][CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][N:22]4[C:31]5[C:26](=[CH:27][CH:28]=[C:29]([O:32][CH3:33])[CH:30]=5)[CH:25]=[CH:24][C:23]4=[O:34])[CH2:16][CH2:15]3)=[CH:11][C:6]=2[O:5][CH2:4][CH2:3]1>[Pd].CO>[ClH:1].[O:2]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][NH:13][CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][N:22]4[C:31]5[C:26](=[CH:27][CH:28]=[C:29]([O:32][CH3:33])[CH:30]=5)[CH2:25][CH2:24][C:23]4=[O:34])[CH2:16][CH2:15]3)=[CH:11][C:6]=2[O:5][CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 67539481HCID 67539481, compound

Product 1

HCID 675390441-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-3,4-dihydroquinolin-2(1H)-one hydrochlorideYield 135.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
47.5 °C

Procedure

To 15 mL of a methanol solution containing 0.11 g of 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxyquinolin-2(1H)-one hydrochloride, 50 mg of 10% palladium on carbon was added, and stirred under hydrogen atmosphere at 45-50° C. for 8.5 hours. The insoluble material was filtered off, the solvent was removed under reduced pressure to afford 0.15 g of 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-3,4-dihydroquinolin-2(1H)-one hydrochloride as a yellow foam.

Workup

  1. additionwas added
  2. filtrationThe insoluble material was filtered off
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-eb8dd1bef8444bbab5bf603eca3919c6
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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