1,4-Dioxane hydrochloride → 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-6-isopropylquinolin-2(1H)-one hydrochloride

HRID 39877Notes

Reaction equation

HRID 39877 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][N:12]([CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[CH:33][C:34]([CH:38]([CH3:40])[CH3:39])=[CH:35][CH:36]=5)[CH:31]=[CH:30][C:29]4=[O:41])[CH2:22][CH2:21]3)C(=O)OC(C)(C)C)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[ClH:42].O1CCOCC1>O1CCOCC1>[ClH:42].[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:12][CH:20]3[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[CH:33][C:34]([CH:38]([CH3:39])[CH3:40])=[CH:35][CH:36]=5)[CH:31]=[CH:30][C:29]4=[O:41])[CH2:24][CH2:25]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59398098HCID 59398098, compound

Product 1

HCID 675395741-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-6-isopropylquinolin-2(1H)-one hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 0.24 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(6-isopropyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 6 mL of 1,4-dioxane and 2 mL of 4.0 mol/L hydrogen chloride/1,4-dioxane were added, and stirred at room temperature overnight. The solvent was removed under reduced pressure, and the resulting solid was recrystallized in methanol-ethyl acetate to give 91 mg of 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-6-isopropylquinolin-2(1H)-one hydrochloride as a white solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting solid was recrystallized in methanol-ethyl acetate

Sources & evidence

ORD record
ord-f802f1687b4347c2b753b23ae16c6a73
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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