Sodium Bicarbonate → HCID 67540253, compound

HRID 39852Notes

Reaction equation

HRID 39852 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:24])=[CH:8][C:9](=[O:23])[N:10]2[CH2:13][CH2:14][C:15]2([C:21]#[N:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:5][CH:4]=1.[O:25]1[CH2:30][CH2:29][O:28][C:27]2[CH:31]=[C:32]([CH2:35][CH:36]=O)[CH:33]=[CH:34][C:26]1=2.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.O.ClCCl.C(O)(=O)C.CO>[O:25]1[C:26]2[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][N:18]3[CH2:19][CH2:20][C: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]([CH3:24])=[CH:8][C:9]4=[O:23])([C:21]#[N:22])[CH2:16][CH2:17]3)=[CH:31][C:27]=2[O:28][CH2:29][CH2:30]1

Participants

10

Reactant 4

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 17979906HCID 17979906, compound2×HCID 67537705HCID 67537705, compound

Product 1

HCID 67540253HCID 67540253, compoundYield 80.1%

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

To 5 mL of methanol solution containing 0.20 g of 4-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidine-4-carbonitrile, 1.5 mL of dichloromethane solution containing 0.33 g of (2,3-dihydrobenzo[b](1,4)dioxin-6-yl)acetaldehyde and 70 μL of acetic acid were added at room temperature, and stirred at the same temperature for 55 min. 77 mg of sodium cyanoborohydride was added at room temperature, and stirred 1 hour and 50 min, thereafter 0.5 mL of dichloromethane solution containing 0.10 g of (2,3-dihydrobenzo[b](1,4)dioxin-6-yl)acetaldehyde was further added and stirred for 1 hour. To the reaction mixture, water, 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, thereafter 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=99:1-97:3], to give 0.24 g of 1-(2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl)-4-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidine-4-carbonitrile as a white foam.

Workup

  1. additionwere added at room temperature
  2. stirringstirred 1 hour and 50 min
  3. additionwas further added
  4. stirringstirred for 1 hour
  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 flash silica gel column chromatography[gradient elution of chloroform

Sources & evidence

ORD record
ord-2be287d043e149baaf7f71fd0e2f3212
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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