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O-Xylene → 2-(1,8,8-Trimethyl-3-azabicyclo[3.2.1]octyl)-4,6-bis(1,1,2,2-tetramethylpropylamino)-s-triazine

HRID 443766
Notes
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Reaction equation

HRID 443766 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][C:25]12[C:32]([CH3:34])([CH3:33])[CH:29]([CH2:30][CH2:31]1)[CH2:28][NH:27][CH2:26]2.C(N(CC)C(C)C)(C)C.C1(C)C(C)=CC=CC=1>C(OCC)(=O)C.O.ClCCl>[CH3:24][C:25]12[C:32]([CH3:34])([CH3:33])[CH:29]([CH2:30][CH2:31]1)[CH2:28][NH:27][CH:26]2[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 7237O-XyleneHCID 81531DiisopropylethylamineHCID 5365563-Azabicyclo[3.2.1]octane, 1,8,8-trimethyl-, (+)-HCID 155725772-Chloro-4,6-di(2,3,3-trimethyl-2-butyl)amino-s-triazine

Product 1

HCID 705625672-(1,8,8-Trimethyl-3-azabicyclo[3.2.1]octyl)-4,6-bis(1,1,2,2-tetramethylpropylamino)-s-triazine

Reagents, catalysts & solvents

3
HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Seven grams (0.02 mole) of 2-chloro-4,6-bis[(1,1,2,2-tetramethylpropyl)amino]-s-triazine, 31 g. (0.2 mole) of 1,8,8-trimethyl-3-azabicyclo[3.2.1]octane, 7.1 ml. (0.04 mole) of N,N-diisopropylethylamine and xylene are refluxed under an argon atmosphere for 22 hours. After cooling, the reaction is diluted with ethyl acetate and water. The mixture is then washed with water, the organic phase dried over magnesium sulfate, filtered through diatomaceous earth and evaporated in vacuo. Addition of toluene and re-evaporation in vacuo several times gives a solid. This solid is then dissolved in dichloromethane, filtered through Magnesol® and the Magnesol® washed with dichloromethane. Evaporation of the solvent and purification by column chromatography gives 2-(1,8,8-trimethyl-3-azabicyclo[3.2.1]octyl)-4,6-bis(1,1,2,2-tetramethylpropylamino)-s-triazine.

Workup

  1. temperatureAfter cooling
  2. washThe mixture is then washed with water
  3. dry with materialthe organic phase dried over magnesium sulfate
  4. filtrationfiltered through diatomaceous earth
  5. customevaporated in vacuo
  6. additionAddition of toluene and re-evaporation in vacuo several times
  7. customgives a solid
  8. filtrationfiltered through Magnesol®
  9. washthe Magnesol® washed with dichloromethane
  10. customEvaporation of the solvent and purification by column chromatography

Sources & evidence

ORD record
ord-796f72c0aa804be1beb5a1237ed4953f
Source dataset
uspto-grants-1981_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04261892

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes