(3,5-Dimethoxyphenyl)methanamine → 1-(2-(4-((2,4-dimethoxybenzyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one

HRID 39850

Reaction equation

HRID 39850 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:23])=[CH:8][C:9](=[O:22])[N:10]2[CH2:13][CH2:14][CH:15]2[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]2)=[CH:5][CH:4]=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([O:34][CH3:35])[CH:33]=1)CN.[C:36]([BH3-])#[N:37].[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.CO>[CH3:35][O:34][C:32]1[CH:33]=[C:26]([O:25][CH3:24])[CH:27]=[CH:28][C:31]=1[CH2:36][NH:37][CH:18]1[CH2:19][CH2:20][CH:15]([CH2:14][CH2:13][N:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[C:7]([CH3:23])=[CH:8][C:9]2=[O:22])[CH2:16][CH2:17]1

Participants

8

Reactant 4

HCID 420973(3,5-Dimethoxyphenyl)methanamineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 593978507-methoxy-4-methyl-1-(2-(4-oxocyclohexyl)ethyl)quinolin-2(1H)-one

Product 1

HCID 593983001-(2-(4-((2,4-dimethoxybenzyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-oneYield 49.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To 3 mL of methanol solution containing 30 mg of 7-methoxy-4-methyl-1-(2-(4-oxocyclohexyl)ethyl)quinolin-2(1H)-one, 16 mg of 3,5-dimethoxybenzylamine, 8 μL of acetic acid and 9 mg of sodium cyanoborohydride were added, and the mixture was allowed to stand overnight after stirred at room temperature for 1 hour. To the reaction mixture, chloroform and aqueous saturated sodium hydrogen carbonate solution were added, the organic layer was separated, 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 flash silica gel column chromatography [gradient elution of chloroform:methanol=90:10-80:20], to give 22 mg of 1-(2-(4-((2,4-dimethoxybenzyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one as a yellow oil.

Workup

  1. additionwere added
  2. customthe organic layer was separated
  3. washwashed with aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by flash silica gel column chromatography [gradient elution of chloroform:methanol=90:10-80:20]

Sources & evidence

ORD record
ord-c833902d0eca4ab093476c7ddb065c58
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Linked notes

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