2,2,6,6-Tetramethylpiperidine → HCID 19428508, compound

HRID 1078961Notes

Reaction equation

HRID 1078961 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[CH3:10][C:11]1([CH3:19])[CH2:16][CH2:15][CH2:14][C:13]([CH3:18])([CH3:17])[NH:12]1>CCCCCC>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[N:7]=[C:2]([N:12]2[C:13]([CH3:18])([CH3:17])[CH2:14][CH2:15][CH2:16][C:11]2([CH3:19])[CH3:10])[N:3]=1

Participants

4

Reactant 2

HCID 130352,2,6,6-TetramethylpiperidineHCID 773782,4,6-Trichloropyrimidine

Product 1

HCID 19428508HCID 19428508, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The mixture of 25 g (136.3 mmoles) of 2,4,6-trichloropyrimidine and 46.3 ml (272.6 mmoles) of 2,2,6,6-tetramethylpiperidine is boiled under reflux for 50 hours, then cooled down and suspended in 250 ml of hexane. The insoluble material is filtered off, the filtrate is evaporated and the evaporation residue is distributed between 300 ml of chloroform and 50 ml of 10% sodium hydroxide solution. After separation the organic phase is washed 4 times with 100 ml of water each, then dried and evaporated. The evaporation residue is purified by chromatography by using hexane as eluent. After recrystallization of the obtained product from hexane, the title compound is obtained in a yield of 8.04 g (20.47%), m.p.: 89°-90° C.

Workup

  1. temperatureunder reflux for 50 hours
  2. temperaturecooled down
  3. filtrationThe insoluble material is filtered off
  4. customthe filtrate is evaporated
  5. customAfter separation the organic phase
  6. washis washed 4 times with 100 ml of water each,
  7. customthen dried
  8. customevaporated
  9. customThe evaporation residue is purified by chromatography
  10. customAfter recrystallization of the obtained product from hexane

Sources & evidence

ORD record
ord-1944da39e3974aa59ff733ff36771aa0
Source dataset
uspto-grants-1996_08
Patent number
US05550240

Reaction notes

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