Water → 2,4,6-Trimethylbenzylamine

HRID 987842Notes

Reaction equation

HRID 987842 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[CH2:4]Cl.[N-:12]=[N+]=[N-].[Na+].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CS(C)=O>[CH3:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[CH2:4][NH2:12]

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 741082,4,6-Trimethylbenzyl chloride

Product 1

HCID 4584332,4,6-TrimethylbenzylamineYield 61%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2,4,6-trimethylbenzyl chloride (5 g, 29.7 mmol) in DMSO (20 mL) was added sodium azide (2.9 g, 44.6 mmol). The mixture was heated at 60° C. for 3 h before it was allowed to cool to rt and poured to water (200 mL). The resulted precipitate was filtered dissolved in wet THF (50 mL) followed by the addition of triphenylphosphine (15.6, 59.4 mmol). The mixture was heated under reflux for 3 h and the volatiles were evaporated. The residue was added to 1 N HCl (200 mL) and the solids were filtered off. The filtrate was basified and the resulted precipitate was filtered, dried under vacuum to give 2,4,6-trimethylbenzylamine (2.7 g, 61% yleld).

Workup

  1. temperatureto cool to rt
  2. filtrationThe resulted precipitate was filtered
  3. dissolutiondissolved in wet THF (50 mL)
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for 3 h
  6. customthe volatiles were evaporated
  7. additionThe residue was added to 1 N HCl (200 mL)
  8. filtrationthe solids were filtered off
  9. filtrationthe resulted precipitate was filtered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-8d1ed2bc05cb4ce288759b6ddee84e71
Source dataset
uspto-grants-2003_10
Patent number
US06632829B2

Reaction notes

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