Propylene Oxide → N-methyl-N-(2-hydroxypropyl)-p-toluidine

HRID 1952983Notes

Reaction equation

HRID 1952983 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.[CH2:10]1[O:13][CH:11]1[CH3:12]>CO>[CH3:1][N:2]([CH2:10][CH:11]([OH:13])[CH3:12])[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6378Propylene OxideHCID 12165Benzenamine, N,4-dimethyl-

Product 1

HCID 23500965N-methyl-N-(2-hydroxypropyl)-p-toluidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-methyl-p-toluidine, 29.3 g, and methanol, 50 g, were placed in a reactor. Propylene oxide, 25.4 g, was slowly added to the reactor over two hours. Afterwards, the reactor was heated under reflux for 6 hours. The low boilers were removed by distillation. Then, the mixture was vacuum distilled to give 2HPMT. The boiling point is 92° C. at 5 mm Hg.

Workup

  1. temperatureAfterwards, the reactor was heated
  2. temperatureunder reflux for 6 hours
  3. customThe low boilers were removed by distillation
  4. distillationdistilled
  5. customto give 2HPMT

Sources & evidence

ORD record
ord-cdebb6e4af4f4c5fbb5fbaf29354e0a5
Source dataset
uspto-grants-2000_09
Patent number
US06114470

Reaction notes

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