4-Pyridinecarboxaldehyde → (+/-)-7-(4-Pyridylmethyleneamino)-1,2,3,5,6,7,8,8a-octahydroindolizine

HRID 9873

Reaction equation

HRID 9873 reaction equation
[NH2:1][CH:2]1[CH2:10][CH:9]2[N:5]([CH2:6][CH2:7][CH2:8]2)[CH2:4][CH2:3]1.[CH:11]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)=O.S([O-])([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1>[N:16]1[CH:17]=[CH:18][C:13]([CH:11]=[N:1][CH:2]2[CH2:10][CH:9]3[N:5]([CH2:6][CH2:7][CH2:8]3)[CH2:4][CH2:3]2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21988494Octahydroindolizin-7-amine

Product 1

HCID 21988493(+/-)-7-(4-Pyridylmethyleneamino)-1,2,3,5,6,7,8,8a-octahydroindolizineYield 100.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

(±)-7-Amino-1,2,3,5,6,7,8,8a-octahydroindolizine (4.91 g (35.0 mmol), prepared as described in 1)) was dissolved in toluene (95 ml). To the solution were added 4-formylpyridine (3.34 ml, 35.0 mmol) and anhydrous magnesium sulfate (3.75 g, 31.2 mmol), and the resulting mixture was stirred at 70° C. for 3 hours. At the end of this time, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated by evaporation under reduced pressure, to give the title compound (8.08 g) as a pale yellow oil (yield quantitative).

Workup

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-48980c3bc29d442994e424cd77e71dc8
Source dataset
uspto-grants-2006_08
Patent number
US07091352B2

Linked notes

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