Ethanolamine → 2,4-Bis {N-[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]butylamino}-6-(2-hydroxyethyl)amino-s-triazine

HRID 650428Notes

Reaction equation

HRID 650428 reaction equation
[OH:1][C:2]([CH3:49])([CH3:48])[CH2:3][O:4][N:5]1[C:10]([CH3:12])([CH3:11])[CH2:9][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]2[N:23]=[C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]3[CH2:34][C:33]([CH3:36])([CH3:35])[N:32]([O:37][CH2:38][C:39]([CH3:42])([OH:41])[CH3:40])[C:31]([CH3:44])([CH3:43])[CH2:30]3)[N:21]=[C:20](Cl)[N:19]=2)[CH2:7][C:6]1([CH3:47])[CH3:46].[CH2:50]([CH2:52][NH2:53])[OH:51].[OH-].[Na+]>>[OH:1][C:2]([CH3:49])([CH3:48])[CH2:3][O:4][N:5]1[C:10]([CH3:12])([CH3:11])[CH2:9][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]2[N:23]=[C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]3[CH2:34][C:33]([CH3:36])([CH3:35])[N:32]([O:37][CH2:38][C:39]([CH3:42])([OH:41])[CH3:40])[C:31]([CH3:44])([CH3:43])[CH2:30]3)[N:21]=[C:20]([NH:53][CH2:52][CH2:50][OH:51])[N:19]=2)[CH2:7][C:6]1([CH3:47])[CH3:46]

Participants

4

Reactant 3

HCID 700EthanolamineHCID 14798Sodium HydroxideHCID 571517592,4-Bis{N-[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]butylamino}-6-chloro-s-triazine

Product 1

HCID 179307792,4-Bis {N-[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]butylamino}-6-(2-hydroxyethyl)amino-s-triazine

Procedure

The title compound is prepared by the reaction of the intermediate prepared in Example 11 with ethanolamine and sodium hydroxide. The aqueous layer is removed, and the remaining layer is extracted with cyclohexane. Solvent is evaporated at reduced pressure, and the crude product is purified by flash chromatography on silica gel with 1:2 (v/v) hexane/ethyl acetate to afford 4.1 g of the title compound as a white solid, melting at 110-120° C.

Workup

  1. customThe aqueous layer is removed
  2. extractionthe remaining layer is extracted with cyclohexane
  3. customSolvent is evaporated at reduced pressure
  4. customthe crude product is purified by flash chromatography on silica gel with 1:2 (v/v) hexane/ethyl acetate

Sources & evidence

ORD record
ord-da7e43fa67cd4835ad1eed884dbafa60
Source dataset
uspto-grants-2001_08
Patent number
US06271377B1

Reaction notes

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