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

HRID 1588971Notes

Reaction equation

HRID 1588971 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-b0834ac3418946d9a046cd9081bfe01f
Source dataset
uspto-grants-1993_06
Patent number
US05223623

Reaction notes

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