Potassium Hydroxide → 3,4,4-Trimethoxypiperidine

HRID 345551Notes

Reaction equation

HRID 345551 reaction equation
[CH3:1][O:2][CH:3]1[C:8]([O:11][CH3:12])([O:9][CH3:10])[CH2:7][CH2:6][N:5](C(OCC)=O)[CH2:4]1.[OH-].[K+]>CC(O)C>[CH3:1][O:2][CH:3]1[C:8]([O:11][CH3:12])([O:9][CH3:10])[CH2:7][CH2:6][NH:5][CH2:4]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 3019431Ethyl 3,4,4-trimethoxypiperidine-1-carboxylate

Product 1

HCID 198835163,4,4-TrimethoxypiperidineYield 75.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of 117.7 parts of ethyl 3,4,4-trimethoxy-1-piperidinecarboxylate, 267.3 parts of potassium hydroxide and 720 parts of 2-propanol was stirred and refluxed for 4 hours. The reaction mixture was evaporated. 900 Parts of water were added to the residue and the whole was stirred in a boiling water-bath. The last traces of 2-propanol were removed by evaporation on a Rotavapor. After cooling to 10° C., the product was extracted twice with 280 parts of 1,1'-oxybisethane. The extracts were dried, filtered and evaporated, yielding 62.9 parts (75.4%) of 3,4,4-trimethoxypiperidine as a residue (intermediate 65).

Workup

  1. temperaturerefluxed for 4 hours
  2. customThe reaction mixture was evaporated
  3. addition900 Parts of water were added to the residue
  4. stirringthe whole was stirred in a boiling water-bath
  5. customThe last traces of 2-propanol were removed by evaporation on a Rotavapor
  6. extractionthe product was extracted twice with 280 parts of 1,1'-oxybisethane
  7. customThe extracts were dried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-26e7b1890dcc4bdc808c5aa8530724f5
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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