Sodium Bicarbonate → 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-4-methylpiperidin-1-yl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one

HRID 39776Notes

Reaction equation

HRID 39776 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:12][C:13]3([CH3:19])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[CH3:20][O:21][C:22]1[CH:31]=[C:30]2[C:25]([C:26]([CH3:36])=[CH:27][C:28](=[O:35])[N:29]2[CH2:32][CH:33]=O)=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:12][C:13]3([CH3:19])[CH2:14][CH2:15][N:16]([CH2:33][CH2:32][N:29]4[C:30]5[C:25](=[CH:24][CH:23]=[C:22]([O:21][CH3:20])[CH:31]=5)[C:26]([CH3:36])=[CH:27][C:28]4=[O:35])[CH2:17][CH2:18]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59397837(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehydeHCID 59398095N-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-methylpiperidine-4-amine

Product 1

HCID 593978651-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-4-methylpiperidin-1-yl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-oneYield 92.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To 2 mL of dichloromethane solution containing 77 mg of N-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-methylpiperidine-4-amine, 68 mg of (7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde and 17 μL of acetic acid were added and stirred at room temperature for 1 hour. To the reaction mixture, 93 mg of sodium triacetoxyborohydride was added and stirred at the same temperature for 30 min. 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 sequentially with water and 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 [eluent; chloroform:methanol=5:1] to give 0.13 g of 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-4-methylpiperidin-1-yl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one as a colorless oil.

Workup

  1. additionwere added
  2. stirringstirred at the same temperature for 30 min
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with chloroform
  5. washwashed sequentially with water and aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=5:1]

Sources & evidence

ORD record
ord-5e4ca8f422ae43e28b155b50e19d51ea
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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