Acetic Acid → HCID 86653282, compound

HRID 2389271Notes

Reaction equation

HRID 2389271 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6](=[O:13])[N:7]2[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]2)=O.[N:19]1([C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=2)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(O)(=O)C.ClC(Cl)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[C:29]([C:28]1[CH:27]=[CH:26][C:25]([N:19]2[CH2:24][CH2:23][N:22]([CH2:1][C:3]3[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6](=[O:13])[N:7]4[C:12]=3[CH:11]=[CH:10][CH:9]=[CH:8]4)[CH2:21][CH2:20]2)=[CH:32][CH:31]=1)#[N:30]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 27339954-(Piperazin-1-yl)benzonitrileHCID 5049666Sodium triacetoxyborohydrideHCID 20634151Ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylate

Product 1

HCID 86653282HCID 86653282, compound

Procedure

A mixture of the ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylate (0.891 g, 3.63 mmol), 4-piperazin-1-ylbenzonitrile (0.952 g, 5.09 mmol), glacial acetic acid (1.25 mL, 21.8 mmol) and 18.2 mL of dichloroethane was stirred vigorously. To the stirring mixture was added sodium triacetoxyborohydride (1.08 g, 5.09 mmol), which was stirred for 18 hours. The mixture was quenched with a 10% sodium carbonate solution, extracted with dichloromethane (1×40 mL), and partitioned between water and dichloromethane. The organic layer was dried over sodium sulfate, filtered, concentrated, and purified by silica gel chromatography eluting with EtOAc to yield ethyl 1-{[4-(4-cyanophenyl)piperazin-1-yl]methyl}-4-oxo-4H-quinolizine-3-carboxylate.

Workup

  1. stirringwas stirred for 18 hours
  2. customThe mixture was quenched with a 10% sodium carbonate solution
  3. extractionextracted with dichloromethane (1×40 mL)
  4. custompartitioned between water and dichloromethane
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography
  9. washeluting with EtOAc

Sources & evidence

ORD record
ord-2beee253c11546ec9bddb758758da7bd
Source dataset
uspto-grants-2012_09
Patent number
US08273737B2

Reaction notes

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