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Triethylenetetramine → HCID 86738307, compound

HRID 2059105
Notes
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Reaction equation

HRID 2059105 reaction equation
[OH:1][CH:2]([CH:26]1[CH2:31][C:30]([CH3:33])([CH3:32])[NH:29][C:28]([CH3:35])([CH3:34])[CH2:27]1)[CH2:3][NH:4][C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH:13]([CH:15]2[CH2:20][C:19]([CH3:22])([CH3:21])[NH:18][C:17]([CH3:24])([CH3:23])[CH2:16]2)[OH:14])[N:8]=[C:7](Cl)[N:6]=1.[NH2:36][CH2:37][CH2:38][NH:39][CH2:40][CH2:41][NH:42][CH2:43][CH2:44][NH2:45].[OH-:46].[Na+]>O1CCOCC1.O>[OH:1][CH:2]([CH:26]1[CH2:31][C:30]([CH3:33])([CH3:32])[NH:29][C:28]([CH3:35])([CH3:34])[CH2:27]1)[CH2:3][NH:4][C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH:13]([CH:15]2[CH2:20][C:19]([CH3:22])([CH3:21])[NH:18][C:17]([CH3:24])([CH3:23])[CH2:16]2)[OH:14])[N:8]=[C:7]([NH:36][CH2:37][CH2:38][N:39]([C:7]2[N:8]=[C:9]([NH:11][CH2:12][CH:13]([CH:15]3[CH2:16][C:17]([CH3:24])([CH3:23])[NH:18][C:19]([CH3:21])([CH3:22])[CH2:20]3)[OH:14])[N:10]=[C:5]([NH:4][CH2:3][CH:2]([CH:26]3[CH2:27][C:28]([CH3:35])([CH3:34])[NH:29][C:30]([CH3:33])([CH3:32])[CH2:31]3)[OH:1])[N:6]=2)[CH2:40][CH2:41][N:42]([C:7]2[N:8]=[C:9]([NH:11][CH2:12][CH:13]([CH:15]3[CH2:16][C:17]([CH3:24])([CH3:23])[NH:18][C:19]([CH3:21])([CH3:22])[CH2:20]3)[OH:14])[N:10]=[C:5]([NH:4][CH2:3][CH:2]([CH:26]3[CH2:27][C:28]([CH3:35])([CH3:34])[NH:29][C:30]([CH3:33])([CH3:32])[CH2:31]3)[OH:1])[N:6]=2)[CH2:43][CH2:44][NH:45][C:7]2[N:8]=[C:9]([NH:11][CH2:12][CH:13]([CH:15]3[CH2:20][C:19]([CH3:22])([CH3:21])[NH:18][C:17]([CH3:23])([CH3:24])[CH2:16]3)[OH:46])[N:10]=[C:5]([NH:4][CH2:3][CH:2]([CH:26]3[CH2:27][C:28]([CH3:35])([CH3:34])[NH:29][C:30]([CH3:33])([CH3:32])[CH2:31]3)[OH:1])[N:6]=2)[N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 5565TriethylenetetramineHCID 14798Sodium HydroxideHCID 867383042,4-Bis{2-hydroxy-N-(2,2,6,6-tetramethyl-4-piperidyl)ethylamino}-6-chloro-1,3,5-triazine

Product 1

HCID 86738307HCID 86738307, compound

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 312751,4-DioxaneSolvent

Procedure

2,4-Bis{2-hydroxy-N-(2,2,6,6-tetramethyl-4-piperidyl)ethylamino}-6-chloro-1,3,5-triazine (8.0 g) and triethylenetetramine (0.5 g) were dissolved in dioxane (100 ml) and to the solution was added an aqueous solution of sodium hydroxide (0.7 g) in water (10 ml). The mixture was heated to reflux for 6 hours. Dioxane was distilled off from the reaction mixture and the residue was extracted with benzene. The extract was treated with silica gel column chromatography (eluent=ethyl acetate:benzene:ethanol:triethylamine=20:4:2:1) to give the desired product as white crystals melting at 158° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 hours
  3. distillationDioxane was distilled off from the reaction mixture
  4. extractionthe residue was extracted with benzene
  5. additionThe extract was treated with silica gel column chromatography (eluent=ethyl acetate:benzene:ethanol:triethylamine=20:4:2:1)

Sources & evidence

ORD record
ord-b27f0edc11d948079e1ba986925693d5
Source dataset
uspto-grants-1982_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04321374

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes