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Hexamethylenediamine → HCID 86738305, compound

HRID 2059103
Notes
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Reaction equation

HRID 2059103 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][CH2:39][CH2:40][CH2:41][CH2:42][NH2:43]>C1(C)C(C)=CC=CC=1>[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][CH2:39][CH2:40][CH2:41][CH2:42][NH:43][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: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)[N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 16402HexamethylenediamineHCID 867383042,4-Bis{2-hydroxy-N-(2,2,6,6-tetramethyl-4-piperidyl)ethylamino}-6-chloro-1,3,5-triazine

Product 1

HCID 86738305HCID 86738305, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2,4-Bis{2-hydroxy-N-(2,2,6,6-tetramethyl-4-piperidyl)ethylamino}-6-chloro-1,3,5-triazine (20.5 g) and hexamethylenediamine (2.0 g) were dissolved in xylene (700 ml), and the mixture was refluxed for 12 hours. The xylene was distilled off from the reaction mixture, and the residue was put into aqueous ammonia, extracted with chloroform and dried over anhydrous magnesium sulfate. The residue obtained by removing the chloroform was chromatographed through silica gel (eluent=ethyl acetate:triethylamine:ethanol=5:1:5), giving the desired product as white crystals with a melting point of 165°-168° C.

Workup

  1. temperaturethe mixture was refluxed for 12 hours
  2. distillationThe xylene was distilled off from the reaction mixture
  3. extractionextracted with chloroform
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residue obtained
  6. customby removing the chloroform
  7. customwas chromatographed through silica gel (eluent=ethyl acetate:triethylamine:ethanol=5:1:5)

Sources & evidence

ORD record
ord-34741d4cc0464ae48fb8ffc0e5338f9d
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