Sodium ethoxide → 2-ethoxy-4,6-bis[N-(2,2,6,6-tetramethyl-4-piperidinyl)butylamino]-1,3,5-triazine

HRID 1955966Notes

Reaction equation

HRID 1955966 reaction equation
[CH3:1][CH2:2][O-:3].[Na+].[CH3:5][C:6]1([CH3:41])[CH2:11][CH:10]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]2[N:22]=[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]3[CH2:33][C:32]([CH3:35])([CH3:34])[NH:31][C:30]([CH3:37])([CH3:36])[CH2:29]3)[N:20]=[C:19](Cl)[N:18]=2)[CH2:9][C:8]([CH3:40])([CH3:39])[NH:7]1>C1(C)C=CC=CC=1>[CH2:2]([O:3][C:19]1[N:20]=[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]2[CH2:33][C:32]([CH3:34])([CH3:35])[NH:31][C:30]([CH3:37])([CH3:36])[CH2:29]2)[N:22]=[C:17]([NH:16][CH2:15][CH2:14][CH2:13][CH2:12][CH:10]2[CH2:9][C:8]([CH3:40])([CH3:39])[NH:7][C:6]([CH3:41])([CH3:5])[CH2:11]2)[N:18]=1)[CH3:1]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 190733162-chloro-4,6-bis[N-(2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazine

Product 1

HCID 675911962-ethoxy-4,6-bis[N-(2,2,6,6-tetramethyl-4-piperidinyl)butylamino]-1,3,5-triazineYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

g)1. 63.5 g (0. 195 mol) of a 21% solution of sodium ethylate in toluene are added dropwise at room temperature under nitrogen to a solution of 69.7 g (0.13 mol) of 2,4-bis[N-(2,2,6,6-tetramethyl-4-piperidinyl)butylamino]-6-chloro-1,3,5-triazine [EP-A-314 472, Sankyo] in 400 ml of toluene. The reaction mixture is then refluxed for 20 hours. After cooling to room temperature, the reaction mixture is washed successively with water, 1N sodium hydrogen carbonate solution and saturated sodium chloride solution. The organic phases are combined, dried over potassium carbonate and concentrated on a vacuum rotary evaporator. Crystallisation of the residue from acetonitrile gives 52.2 g (74%) of 2-ethoxy-4,6-bis[N-(2,2,6,6-tetramethyl-4-piperidinyl)butylamino]-1,3,5-triazine, m.p. 95°-104° C., in the form of a white powder. 1H-NMR (300 MHz, CDCl3): δ=4.345 ppm (q, J=7 Hz) --OCH2CH3.

Workup

  1. temperatureThe reaction mixture is then refluxed for 20 hours
  2. washthe reaction mixture is washed successively with water, 1N sodium hydrogen carbonate solution and saturated sodium chloride solution
  3. dry with materialdried over potassium carbonate
  4. concentrationconcentrated on a vacuum rotary evaporator
  5. customCrystallisation of the residue from acetonitrile

Sources & evidence

ORD record
ord-1134b3e149cf4673bc049b240c0e17ac
Source dataset
uspto-grants-1998_07
Patent number
US05777113

Reaction notes

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