1,4-Benzenedimethanamine → HCID 86738306, compound

HRID 2059104Notes

Reaction equation

HRID 2059104 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.[C:36]1([CH2:44][NH2:45])[CH:41]=[CH:40][C:39]([CH2:42][NH2:43])=[CH:38][CH:37]=1>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:43][CH2:42][C:39]2[CH:40]=[CH:41][C:36]([CH2:44][NH:45][C:7]3[N:8]=[C:9]([NH:11][CH2:12][CH:13]([CH:15]4[CH2:20][C:19]([CH3:22])([CH3:21])[NH:18][C:17]([CH3:23])([CH3:24])[CH2:16]4)[OH:14])[N:10]=[C:5]([NH:4][CH2:3][CH:2]([CH:26]4[CH2:27][C:28]([CH3:35])([CH3:34])[NH:29][C:30]([CH3:33])([CH3:32])[CH2:31]4)[OH:1])[N:6]=3)=[CH:37][CH:38]=2)[N:6]=1

Participants

4

Reactant 2

HCID 683151,4-BenzenedimethanamineHCID 867383042,4-Bis{2-hydroxy-N-(2,2,6,6-tetramethyl-4-piperidyl)ethylamino}-6-chloro-1,3,5-triazine

Product 1

HCID 86738306HCID 86738306, 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 (15.4 g) and p-xylylenediamine (1.4 g) were dissolved in xylene (50 ml) and the solution was heated to reflux for 5 hours. The reaction mixture was poured into ice water. After saturation with potassium carbonate, the mixture was extracted with a mixture of benzene (300 ml) and chloroform (500 ml). The extract was dried over anhydrous potassium carbonate and benzene and chloroform were distilled off. The resulting residue was treated with silica gel column chromatography (eluent=ethyl acetate:triethylamine:ethanol=3:1:1) to yield crystals, which were recrystallized from cyclohexane to give the desired product with a melting point of 151°-156° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 5 hours
  3. extractionAfter saturation with potassium carbonate, the mixture was extracted with a mixture of benzene (300 ml) and chloroform (500 ml)
  4. dry with materialThe extract was dried over anhydrous potassium carbonate and benzene and chloroform
  5. distillationwere distilled off
  6. additionThe resulting residue was treated with silica gel column chromatography (eluent=ethyl acetate:triethylamine:ethanol=3:1:1)
  7. customto yield crystals, which
  8. customwere recrystallized from cyclohexane

Sources & evidence

ORD record
ord-501d09a5556148c89bce40828176d416
Source dataset
uspto-grants-1982_03
Patent number
US04321374

Reaction notes

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