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

HRID 728915
Notes
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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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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. custom
Triturate the solid with 100 mL of ethanol
  • filtrationfilter the solid
  • washwash with ethanol
  • Sources & evidence

    ORD record
    ord-ea00a29a82bd4dcab40ac011449b56ee
    Source dataset
    uspto-grants-1991_09
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US05051422

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes