Diethyl Ether → N-(2,6-dimethylphenyl)-1-methyl-4-piperidinamine

HRID 236759Notes

Reaction equation

HRID 236759 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O(CC)CC.[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=1[NH:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27](OCC)=O)[CH2:23][CH2:22]1>O>[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=1[NH:20][CH:21]1[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 21226445Aluminium lithium hydrideHCID 23338990HCID 23338990, compound

Product 1

HCID 23339018N-(2,6-dimethylphenyl)-1-methyl-4-piperidinamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

To a stirred and refluxing suspension of 2 parts of lithium aluminiumhydride in 120 parts of 1,1'-oxybisethane is added dropwise a solution of 13 parts of ethyl 4-[N-(2,6-dimethylphenyl)amino]-1-piperidinecarboxylate in 40 parts of 1,1'-oxybisethane. After the addition is complete, stirring and refluxing is continued for 20 hours. The reaction mixture is cooled to 5° C. and 7 parts of water are added. The formed precipitate is filtered off, washed on the filter with 1,1'-oxybisethane and the filtrate is evaporated. The oily residue is distilled, yielding 5.8 parts of N-(2,6-dimethylphenyl)-1-methyl-4-piperidinamine; bp. 90°-93° C. at 0.003 mm. pressure. On standing the distillate solidifies, to yield solid N-(2,6-dimethylphenyl)-1-methyl-4-piperidinamine with a melting point of 45° C.

Workup

  1. temperaturerefluxing
  2. additionAfter the addition
  3. stirringstirring
  4. temperaturerefluxing
  5. filtrationThe formed precipitate is filtered off
  6. washwashed on the
  7. filtrationfilter with 1,1'-oxybisethane
  8. customthe filtrate is evaporated
  9. distillationThe oily residue is distilled

Sources & evidence

ORD record
ord-f1b4f966aaae41a8b4793017ccade9b0
Source dataset
uspto-grants-1979_06
Patent number
US04157393

Reaction notes

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