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 1356909Notes

Reaction equation

HRID 1356909 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-72ac14ab6c5a44d3b0047e1e25cc10d9
Source dataset
uspto-grants-2003_07
Patent number
US06586507B2

Reaction notes

Loading…