Sodium Hydroxide → Dimethyl[2-methyl-2-(piperidin-4-yl)propyl]amine

HRID 977164Notes

Reaction equation

HRID 977164 reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][C:4]([CH3:12])([CH3:11])[C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1.[H][H].[OH-].[Na+]>C(O)(=O)C.[Pt](=O)=O>[CH3:13][N:2]([CH3:1])[CH2:3][C:4]([CH3:11])([CH3:12])[CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 11805314HCID 11805314, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10921200Dimethyl[2-methyl-2-(piperidin-4-yl)propyl]amineYield 93.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2 g (1.1×10-2 mole ) of N,N,β,β-tetramethyl-4-pyridineethanamine in 400 ml of acetic acid was hydrogenated in a Parr's apparatus at 50° C. at a hydrogen pressure of 3.106Pa in the presence of platinum dioxide. After eliminating the catalyst by filtering, the solvents were evaporated off under reduced pressure. The residue obtained was taken up in an aqueous 30% sodium hydroxide solution and extracted with methylene chloride. The organic phase was washed, dried over magnesium sulphate and filtered and the solvents were evaporated off under reduced pressure. 1.9 g (yield: 92%) of the desired compound was obtained as an oil. B Pt=60°-64° C. under 0.02 mm Hg (i.e. about 2.66 Pa)

Workup

  1. filtrationby filtering
  2. customthe solvents were evaporated off under reduced pressure
  3. customThe residue obtained
  4. extractionextracted with methylene chloride
  5. washThe organic phase was washed
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvents were evaporated off under reduced pressure

Sources & evidence

ORD record
ord-01b832c0f59d4c49b579fea147d602f8
Source dataset
uspto-grants-1997_03
Patent number
US05614534

Reaction notes

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