5-Chloro-2-methylaniline → N'-(5-Chloro-2-methyl-phenyl)-N-ethyl-propane-1,3-diamine

HRID 1250879Notes

Reaction equation

HRID 1250879 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)[NH2:7].Br.[CH2:11]([NH:13][CH2:14][CH2:15][CH2:16]Br)[CH3:12]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([NH:7][CH2:16][CH2:15][CH2:14][NH:13][CH2:11][CH3:12])[CH:8]=1

Participants

4

Reactant 2

HCID 72605-Chloro-2-methylanilineHCID 183248271-Propanamine, 3-bromo-N-ethyl-, hydrobromide

Product 1

HCID 18324842N'-(5-Chloro-2-methyl-phenyl)-N-ethyl-propane-1,3-diamineYield 92.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-chloro-2-methylaniline (12.3 g) and the N-ethyl-1-amino-3-bromopropane hydrobromide salt of Example 3, Step C (8.6 g) was heated at 100° C. under nitrogen for 20 minutes. After cooling, a solid mass formed which was partitioned between dichloromethane and 1 N sodium hydroxide. The organic phase was washed with brine, dried over anhydrous potassium carbonate, filtered and concentrated in vacuo to give a brown oil. The crude material was dissolved in dichloromethane and absorbed onto a column of Merck-60 flash silica gel. Elution with a solvent gradient (from 100% dichloromethane to 9:1 dichloromethane-methanol containing 0.2% ammonium hydroxide) provided the title compound (7.3 g, 92.8%) as a brown oil, which was used as such in the next step.

Workup

  1. temperatureAfter cooling
  2. customa solid mass formed which
  3. customwas partitioned between dichloromethane and 1 N sodium hydroxide
  4. washThe organic phase was washed with brine
  5. dry with materialdried over anhydrous potassium carbonate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a brown oil
  9. customabsorbed onto a column of Merck-60 flash silica gel
  10. washElution with a solvent gradient (from 100% dichloromethane to 9:1 dichloromethane-methanol containing 0.2% ammonium hydroxide)

Sources & evidence

ORD record
ord-d6c3e020775249ccbffb81433f414dd9
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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