Potassium Iodide → N-(2,6-dimethylphenyl)-1-propyl-4-piperidinamine

HRID 28143Notes

Reaction equation

HRID 28143 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].I[CH2:25][CH2:26][CH3:27]>O.C1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:25][CH2:26][CH3:27])[CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 336431-IodopropaneHCID 23339004N-(2,6-Dimethylphenyl)piperidin-4-amine

Product 1

HCID 23339025N-(2,6-dimethylphenyl)-1-propyl-4-piperidinamine

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a warm (about 40° C.) and stirred mixture of 5 parts of N-(2,6-dimethylphenyl)-4-piperidinamine, 5 parts of sodium carbonate, a few crystals of potassium iodide in 120 parts of benzene is added dropwise a solution of 5.1 parts of 1-iodopropane in 80 parts of benzene. After the addition is complete, stirring is continued for 40 hours at reflux temperature. The reaction mixture is cooled and 50 parts of water are added. The organic layer is separated, dried and evaporated in vacuo. The oily residue is distilled, yielding 10.2 parts of N-(2,6-dimethylphenyl)-1-propyl-4-piperidinamine; bp. 135° C. at 0.2 mm. pressure.

Workup

  1. additionAfter the addition
  2. stirringstirring
  3. temperatureat reflux temperature
  4. temperatureThe reaction mixture is cooled
  5. customThe organic layer is separated
  6. customdried
  7. customevaporated in vacuo
  8. distillationThe oily residue is distilled

Sources & evidence

ORD record
ord-72a05fb9d5f84632a59fda691ecf743c
Source dataset
uspto-grants-1980_09
Patent number
US04225606

Reaction notes

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