Formic Acid → 3-(1-Methylazetidin-2-yl)pyridine

HRID 261095Notes

Reaction equation

HRID 261095 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:10][CH2:9][NH:8]2)[CH:2]=1.C=O.[CH:13](O)=O.C(=O)(O)[O-].[Na+]>O>[CH3:13][N:8]1[CH2:9][CH2:10][CH:7]1[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 203960983-(Azetidin-2-yl)pyridine

Product 1

HCID 1638273-(1-Methylazetidin-2-yl)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 920 mg (6.88 mmoles) of the 2-(3-pyridyl)azetidine produced in Example 2 in 9 ml of water was added a solution of 660 mg (8.83 mmoles) of formaldehyde (40% w/w) in 9 ml of water and 755 mg (14.5 mmoles) of 88% formic acid in 9 ml of water. After heating on a steam bath for 2 hours, cooling to 0° C. and adding 1.21 g (14.4 mmoles) of sodium bicarbonate, the colored solution was concentrated under reduced pressure to 7 ml. It was then dried by azeotroping in benzene and ethyl alcohol to give a dry benzene solution containing insolubles. These insolubles were then filtered off to yield a solution of N-methyl-2-(3-pyridyl)azetidine.

Workup

  1. temperatureAfter heating on a steam bath for 2 hours
  2. concentrationthe colored solution was concentrated under reduced pressure to 7 ml
  3. customIt was then dried
  4. customby azeotroping in benzene
  5. customethyl alcohol to give a dry benzene solution
  6. additioncontaining insolubles
  7. filtrationThese insolubles were then filtered off

Sources & evidence

ORD record
ord-a7e2a153064f4bd08fabe273b76dfaf9
Source dataset
uspto-grants-1979_08
Patent number
US04163855

Reaction notes

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