Water → 1-(4-(Pyrrolidin-1-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone

HRID 2388696Notes

Reaction equation

HRID 2388696 reaction equation
[CH:1]1[C:6](=CN=O)[CH:5]=[CH:4][NH:3][CH:2]=1.Cl[N:11]1[C:15](=O)[CH2:14][CH2:13][C:12]1=O.[CH2:18]([O:20]CC)[CH3:19].O>CN(C=O)C>[N:11]1([C:6]2[CH2:1][CH2:2][N:3]([C:18](=[O:20])[CH3:19])[CH2:4][CH:5]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 31398ChlorosuccinimideHCID 178526339HCID 178526339, compound

Product 1

HCID 141055951-(4-(Pyrrolidin-1-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Pyridine-4-carbaldoxime (1 g, 8.19 mmol) was dissolved in DMF (10 ml), a solution of N-chlorosuccinimide (1.31 g, 9.83 mmol) in DMF (5 ml) was slowly added dropwise and the reaction mixture was stirred at room temperature. When the reaction was complete (thin layer chromatography control, here 6 h), diethyl ether (50 ml) and water (20 ml) were added, phase separation, extraction of the aqueous phase with diethyl ether (5×30 ml). The combined organic phases were washed with water (50 ml) and saturated sodium chloride solution (50 ml), dried (MgSO4) and concentrated in vacuo. The crude yield was reacted without further purification and analysis. The yield was 0.74 g (>99%).

Workup

  1. customthin layer chromatography control, here 6 h
  2. additionwere added
  3. customphase separation, extraction of the aqueous phase with diethyl ether (5×30 ml)
  4. washThe combined organic phases were washed with water (50 ml) and saturated sodium chloride solution (50 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude yield
  8. customwas reacted without further purification and analysis

Sources & evidence

ORD record
ord-88e1057b11964eab80e71477aefde56c
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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