Methanol → 1-(2-(4-(4-ethylbenzylamino)piperidin-1-yl)ethyl)-7-methoxy-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide

HRID 2193330

Reaction equation

HRID 2193330 reaction equation
CO.[NH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=3)[C:15]([C:24]([NH:26][CH3:27])=[O:25])=[CH:14][C:13]2=[O:28])[CH2:6][CH2:5]1.[CH2:29]([C:31]1[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=1)[CH3:30].C([BH3-])#N.[Na+]>C(O)(=O)C>[CH2:29]([C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH:3][CH:4]2[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][N:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=4)[C:15]([C:24]([NH:26][CH3:27])=[O:25])=[CH:14][C:13]3=[O:28])[CH2:6][CH2:5]2)=[CH:33][CH:32]=1)[CH3:30]

Participants

6

Reactant 4

HCID 887MethanolHCID 208614-EthylbenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 593979881-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide

Product 1

HCID 593980151-(2-(4-(4-ethylbenzylamino)piperidin-1-yl)ethyl)-7-methoxy-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamideYield 82.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 4 mL of a methanol solution containing 0.14 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide, 48 mg of 4-ethylbenzaldehyde and 40 μL of acetic acid were added, and stirred at room temperature for 80 min. To the reaction mixture, 52 mg of sodium cyanoborohydride was added, and stirred at the same temperature for 75 min. After the solvent was removed under reduced pressure, chloroform and aqueous saturated sodium hydrogen carbonate solution were added, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; chloroform:methanol=30:1], to give 0.14 g of 1-(2-(4-(4-ethylbenzylamino)piperidin-1-yl)ethyl)-7-methoxy-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide as a pale yellow solid.

Workup

  1. additionwere added
  2. stirringstirred at the same temperature for 75 min
  3. customAfter the solvent was removed under reduced pressure, chloroform and aqueous saturated sodium hydrogen carbonate solution
  4. additionwere added
  5. customthe organic layer was separated
  6. extractionthe aqueous layer was extracted with chloroform
  7. washwashed with aqueous saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was removed under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; chloroform:methanol=30:1]

Sources & evidence

ORD record
ord-55648d0f488141d9998d77166403b296
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Linked notes

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