1,4-Dioxane hydrochloride → 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-5-acetaminoquinolin-2(1H)-one hydrochloride

HRID 2193302Notes

Reaction equation

HRID 2193302 reaction equation
C(OC(=O)[N:7]([CH2:31][C:32]1[CH:41]=[CH:40][C:35]2[O:36][CH2:37][CH2:38][O:39][C:34]=2[CH:33]=1)[CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[C:25]3[C:20](=[C:21]([NH:26][C:27]([CH3:29])=[O:28])[CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][C:17]2=[O:30])[CH2:10][CH2:9]1)(C)(C)C.[ClH:43].O1CCOCC1>O1CCOCC1>[ClH:43].[O:36]1[C:35]2[CH:40]=[CH:41][C:32]([CH2:31][NH:7][CH:8]3[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]4[C:25]5[C:20](=[C:21]([NH:26][C:27]([CH3:29])=[O:28])[CH:22]=[CH:23][CH:24]=5)[CH:19]=[CH:18][C:17]4=[O:30])[CH2:10][CH2:9]3)=[CH:33][C:34]=2[O:39][CH2:38][CH2:37]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59397911HCID 59397911, compound

Product 1

HCID 675386621-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-5-acetaminoquinolin-2(1H)-one hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 60 mg of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(5-acetamino-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 3 mL of 1,4-dioxane and 1 mL of 4 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 18 mg of 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-5-acetaminoquinolin-2(1H)-one hydrochloride as a pale yellow 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-8d91452f4dac4e3185a4258aabc16e10
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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