Methanol → 2-Methoxy-1-formylpiperidine

HRID 1995269Notes

Reaction equation

HRID 1995269 reaction equation
[CH:1]([N:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)=[O:2].[CH3:9][OH:10]>F[B-](F)(F)F.C[N+](C)(C)C.[Ni]>[CH:1]([N:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:10][CH3:9])=[O:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 174291-PiperidinecarboxaldehydeHCID 178435160HCID 178435160, compound

Product 1

HCID 27236672-Methoxy-1-formylpiperidineYield 84.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 12621Tetramethylammonium tetrafluoroborateCatalyst

Procedure

An electrode assembly consisting of an anode of glassy carbon, a nickel cathode and two bipolar connected electrodes of glassy carbon inserted between the two outer electrodes was fitted in the cell of the device as described in Example 1. All four electrodes were framed as described in Example 1. Polyethylene nets (mesh width 3×5 mm and thickness of filaments 0.5 mm) between the plates had the function of spacers. In this cell, a mixture of 4,800 g of 1-formylpiperidine, 13,600 g of methanol and 68 g of tetramethylammonium tetrafluoroborate was electrolyzed at 27.5 A, 45 volts and 25° C. for 27 hours and 33 minutes (corresponding to 2,273 Ahr). After distillative work up, 5,120 g of 1-formyl-2-methoxypiperidine were isolated, corresponding to a current efficiency of 80.3%.

Workup

  1. customwas fitted in the cell of the device
  2. custom45 volts and 25° C.
  3. customfor 27 hours
  4. custom33 minutes (corresponding to 2,273 Ahr)

Sources & evidence

ORD record
ord-6757a7b9055c41ae8896d4ecf776bc08
Source dataset
uspto-grants-1983_09
Patent number
US04404082

Reaction notes

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