3-Methoxyaniline → N-(3-Methoxyphenyl)-N'-(phenylmethyl)-1,2-ethanediamine hydrochloride

HRID 728915Notes

Reaction equation

HRID 728915 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1.Cl.[Cl:11][CH2:12][CH2:13][NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[ClH:11].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][CH2:12][CH2:13][NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 108243-MethoxyanilineHCID 13054189Benzenemethanamine, N-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 19755023N-(3-Methoxyphenyl)-N'-(phenylmethyl)-1,2-ethanediamine hydrochloride

Procedure

Combine 3-methoxybenzenamine (81.2 g, 0.66 mol) with N-(2-chloroethyl)-benzenemethanamine hydrochloride (45.3 g, 0.22 mol) and heat to 190° C. for 13 h. Add methylene chloride to precipitate a solid. Filter the solid and wash with methylene chloride. Triturate the solid with 100 mL of ethanol, filter the solid and wash with ethanol to give the title compound.

Workup

  1. customAdd methylene chloride to precipitate a solid
  2. filtrationFilter the solid
  3. washwash with methylene chloride
  4. customTriturate the solid with 100 mL of ethanol
  5. filtrationfilter the solid
  6. washwash with ethanol

Sources & evidence

ORD record
ord-ea00a29a82bd4dcab40ac011449b56ee
Source dataset
uspto-grants-1991_09
Patent number
US05051422

Reaction notes

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