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

HRID 2049369Notes

Reaction equation

HRID 2049369 reaction equation
[Li].O(CC)CC.[CH3:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[NH:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22](OCC)=O)[CH2:18][CH2:17]1>O>[CH3:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[NH:15][CH:16]1[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 3028194LithiumHCID 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 aluminumhydride 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-3b3771cc8da94445b7b2bbec632d93cc
Source dataset
uspto-grants-1980_04
Patent number
US04197304

Reaction notes

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