Potassium Iodide → HCID 53917476, compound

HRID 1862802Notes

Reaction equation

HRID 1862802 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]1([CH3:36])[CH2:15][CH:14]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH:24]3[CH2:29][C:28]([CH3:31])([CH3:30])[NH:27][C:26]([CH3:33])([CH3:32])[CH2:25]3)=[CH:19][CH:18]=2)[CH2:13][C:12]([CH3:35])([CH3:34])[NH:11]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(CC)=O>[CH2:1]([N:27]1[C:26]([CH3:33])([CH3:32])[CH2:25][CH:24]([CH2:23][C:20]2[CH:19]=[CH:18][C:17]([CH2:16][CH:14]3[CH2:13][C:12]([CH3:35])([CH3:34])[N:11]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:10]([CH3:36])([CH3:9])[CH2:15]3)=[CH:22][CH:21]=2)[CH2:29][C:28]1([CH3:31])[CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 20393570HCID 20393570, compound

Product 1

HCID 53917476HCID 53917476, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

8.72 g of benzyl bromide were added dropwise in the course of one hour to a mixture of 9.6 g of 1,4-bis-(2,2,6,6-tetramethylpiperidin-4-yl-methyl)-benzene (compound No. 9) 7.6 g of finely powdered potassium carbonate and 0.5 g of potassium iodide in 50 ml of ethyl methyl ketone, at the boil (bath temperature about 100° C.), whilst stirring, and the reaction mixture was stirred at this temperature for a total of 96 hours. For working up, the reaction mixture was filtered at the boiling point to remove the sediment (potassium bromide and a little potassium carbonate) and the filter residue was repeatedly rinsed with dichloromethane. The combined filtrates were freed from the solvent in vacuo, and the crystalline residue was recrystallised from ethyl methyl ketone to yield 1,4-bis(1-benzyl-2,2,6,6-tetramethylpiperidin-4-yl-methyl)-benzene, m.p. 207°-208° C. (compound No. 15).

Workup

  1. stirringthe reaction mixture was stirred at this temperature for a total of 96 hours
  2. filtrationthe reaction mixture was filtered at the boiling point
  3. customto remove the sediment (potassium bromide
  4. washa little potassium carbonate) and the filter residue was repeatedly rinsed with dichloromethane
  5. customthe crystalline residue was recrystallised from ethyl methyl ketone

Sources & evidence

ORD record
ord-aa784694d6064b6db3853abd4e6f1752
Source dataset
uspto-grants-1979_09
Patent number
US04166814

Reaction notes

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