Ethyl Acetate → 7-methoxy-N-methyl-1-(2-(4-((naphthalen-2-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinoline-4-carboxamide hydrochloride

HRID 39950Notes

Reaction equation

HRID 39950 reaction equation
C(OCC)(=O)C.[CH3:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:40]([NH:42][CH3:43])=[O:41])=[CH:14][C:15](=[O:39])[N:16]2[CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([NH:27][CH2:28][C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=3)[CH2:23][CH2:22]2)=[CH:11][CH:10]=1.[ClH:44].C(OCC)(=O)C>CO>[ClH:44].[CH3:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:40]([NH:42][CH3:43])=[O:41])=[CH:14][C:15](=[O:39])[N:16]2[CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH:24]([NH:27][CH2:28][C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=3)[CH2:25][CH2:26]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21866389Hydrogen chloride-ethyl acetateHCID 593983767-methoxy-N-methyl-1-(2-(4-((naphthalen-2-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinoline-4-carboxamide

Product 1

HCID 675386827-methoxy-N-methyl-1-(2-(4-((naphthalen-2-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinoline-4-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixed solution of 1 mL ethyl acetate and 2 mL methanol containing 0.20 g of 7-methoxy-N-methyl-1-(2-(4-((naphthalen-2-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinoline-4-carboxamide, 1 mL of 4 mol/L hydrogen chloride/ethyl acetate was added at room temperature, and the solvent was removed under reduced pressure. Ethyl acetate was added to the residue thus obtained, and the resulting solid was filtered to give 0.16 g of 7-methoxy-N-methyl-1-(2-(4-((naphthalen-2-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinoline-4-carboxamide hydrochloride as a pale yellow solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. customthus obtained
  4. filtrationthe resulting solid was filtered

Sources & evidence

ORD record
ord-199f67b8684346e3953743ba58fce9a7
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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