Sodium Hydroxide → HCID 11823533, compound

HRID 977162Notes

Reaction equation

HRID 977162 reaction equation
[H-].[Na+].COCCO[Al+]OCCOC.[H-].[CH2:15]([N:27]1[CH2:32][CH2:31][CH:30]([C:33]([CH3:38])([CH3:37])[C:34]([NH2:36])=O)[CH2:29][CH2:28]1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[OH-].[Na+]>CC1C=CC=CC=1>[CH2:15]([N:27]1[CH2:28][CH2:29][CH:30]([C:33]([CH3:37])([CH3:38])[CH2:34][NH2:36])[CH2:31][CH2:32]1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15294370HCID 15294370, compoundHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 11823533HCID 11823533, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10 ml of bis(2-methoxyethoxy)aluminium-sodium hydride was added dropwise to a solution of 2.95 g (8.7×10-2 mole) of 1-dodecyl-α,α-dimethyl-4-piperidine-acetamide in 80 ml of methylbenzene. After stirring for one hour at room temperature, the mixture was refluxed for three hours. After cooling the mixture, 50 ml of 3N sodium hydroxide was carefully added and stirring was continued for 24 hours. The resulting mixture was extracted with methylbenzene. The organic phase was washed with water, dried over magnesium sulphate and filtered and the solvents were evaporated off under reduced pressure. The product was purified using silica gel chromatography, eluting with a 4/1/0.1 (v/v/v) ethyl acetate/methanol/ammonia mixture. 1.8 g (yield: 64%) of 1-dodecyl-β,β-dimethyl-4-piperidineethanamine was obtained as an oil. The (E)-2-butenedioate was obtained from this oil in an acetone-ether mixture. M Pt=100°-120° C.

Workup

  1. temperaturethe mixture was refluxed for three hours
  2. additionwas carefully added
  3. stirringstirring
  4. waitwas continued for 24 hours
  5. extractionThe resulting mixture was extracted with methylbenzene
  6. washThe organic phase was washed with water
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customthe solvents were evaporated off under reduced pressure
  10. customThe product was purified
  11. washeluting with a 4/1/0.1 (v/v/v) ethyl acetate/methanol/ammonia mixture

Sources & evidence

ORD record
ord-3a0f8577c45f448da55bcece375501a4
Source dataset
uspto-grants-1997_03
Patent number
US05614534

Reaction notes

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