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

HRID 1078300Notes

Reaction equation

HRID 1078300 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

A mixture containing 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 the reaction mixture is cooled down and suspended in 250 ml of hexane. The insoluble part is filtered off, the filtrate (mother liquor) is evaporated and the 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, dried and evaporated. The residue is purified by chromatography on a silica gel column by using hexane as eluent. After recrystallization from hexane the title compound is obtained in a yield of 8.04 g (20.47%), m.p.:89°-900° C.

Workup

  1. temperatureunder reflux for 50 hours
  2. temperaturethe reaction mixture is cooled down
  3. filtrationThe insoluble part is filtered off
  4. customthe filtrate (mother liquor) is evaporated
  5. customAfter separation the organic phase
  6. washis washed 4 times with 100 ml of water each,
  7. customdried
  8. customevaporated
  9. customThe residue is purified by chromatography on a silica gel column
  10. customAfter recrystallization from hexane the title compound
  11. customis obtained in a yield of 8.04 g (20.47%), m.p.:89°-900° C.

Sources & evidence

ORD record
ord-bd453e60dd59450aafaa2bf95382c6a8
Source dataset
uspto-grants-1996_08
Patent number
US05547949

Reaction notes

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