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Tetrafluoro-m-phenylenediamine dihydrochloride → 2-[4-(p-Methoxyphenyl)-1-piperazinyl]-4,6-bis[(1,1,2,2-tetramethylpropyl)amino]-s-triazine

HRID 2287156
Notes
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Reaction equation

HRID 2287156 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]([CH3:15])([CH3:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[N:5]=[C:4]([NH:16][C:17]([CH3:23])([CH3:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[N:3]=1.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[CH:28][CH:27]=1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>ClC1C=CC=CC=1>[CH3:24][O:25][C:26]1[CH:27]=[CH:28][C:29]([N:32]2[CH2:37][CH2:36][N:35]([C:2]3[N:7]=[C:6]([NH:8][C:9]([CH3:15])([CH3:14])[C:10]([CH3:13])([CH3:11])[CH3:12])[N:5]=[C:4]([NH:16][C:17]([CH3:22])([CH3:23])[C:18]([CH3:19])([CH3:21])[CH3:20])[N:3]=3)[CH2:34][CH2:33]2)=[CH:30][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 2697221-(4-Methoxyphenyl)piperazineHCID 155725772-Chloro-4,6-di(2,3,3-trimethyl-2-butyl)amino-s-triazine

Product 1

HCID 234594992-[4-(p-Methoxyphenyl)-1-piperazinyl]-4,6-bis[(1,1,2,2-tetramethylpropyl)amino]-s-triazine

Reagents, catalysts & solvents 1

HCID 7964
Chlorobenzene
Solvent

Procedure

A mixture of 6.84 g. of 2-chloro-4,6-bis[(1,1,2,2-tetramethylpropyl)amino]-s-triazine and 7.69 g. of N-(p-methoxyphenyl)piperazine (prepared from the commercially available dihydrochloride salt) in 150 ml. of chlorobenzene is refluxed for 5 hours and then cooled. The reaction mixture is washed with two 25 ml. portions of water. The organic layer is dried over anhydrous potassium carbonate and magnesium sulfate and the solvent is stripped with a water pump. The residual amber oil is crystallized by slurrying in isopropanol. Recrystallization from 150 ml. of propanol (using charcoal for decolorization) gives the desired product as a white solid, m.p. 155°-157° C.

Workup

  1. additionA mixture of 6.84 g
  2. temperaturecooled
  3. washThe reaction mixture is washed with two 25 ml
  4. dry with materialThe organic layer is dried over anhydrous potassium carbonate and magnesium sulfate
  5. customThe residual amber oil is crystallized
  6. customRecrystallization from 150 ml

Sources & evidence

ORD record
ord-11fdc509d712497a98bb0c44693b631a
Source dataset
uspto-grants-1981_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04269832

Reaction notes

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