2,3-Dihydro-1,4-benzodioxin-6-methylamine → 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one

HRID 2193222

Reaction equation

HRID 2193222 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.[O:24]1[CH2:29][CH2:28][O:27][C:26]2[CH:30]=[C:31]([CH2:34][NH2:35])[CH:32]=[CH:33][C:25]1=2.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.O.C(O)(=O)C.CO>[O:24]1[C:25]2[CH:33]=[CH:32][C:31]([CH2:34][NH:35][CH:18]3[CH2:17][CH2:16][CH:15]([CH2:14][CH2:13][N:10]4[C:11]5[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=5)[C:7]([CH3:23])=[CH:8][C:9]4=[O:22])[CH2:20][CH2:19]3)=[CH:30][C:26]=2[O:27][CH2:28][CH2:29]1

Participants

9

Reactant 4

HCID 871022,3-Dihydro-1,4-benzodioxin-6-methylamineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 593978507-methoxy-4-methyl-1-(2-(4-oxocyclohexyl)ethyl)quinolin-2(1H)-one

Product 1

HCID 593984071-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-oneYield 28.9%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To 2 mL of methanol solution containing 45 mg of 7-methoxy-4-methyl-1-(2-(4-oxocyclohexyl)ethyl)quinolin-2(1H)-one and 21 mg of (2,3-dihydrobenzo[b][1,4-]dioxin-6-yl)methylamine, 10 μL of acetic acid and 12 mg of sodium cyanoborohydride were added, and stirred at the same temperature for 30 min. To the reaction mixture, water, 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 [eluent; chloroform:methanol=20:1], to give (A) 5.4 mg of 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one as a yellow oil and (B) 17 mg of 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one as a pale yellow foam.

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 [eluent; chloroform:methanol=20:1]

Sources & evidence

ORD record
ord-05126c10c26d460cb360a47c7ba12987
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Linked notes

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