N-(2,6-dimethylphenyl)-ethylenediamine → 1-(4-Propoxyphenoxy)-3-[2-(2,6-dimethylphenylamino)-ethylamino]-propan-2-ol

HRID 365178Notes

Reaction equation

HRID 365178 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH3:15])=[CH:8][CH:7]=1)[CH:2]1[O:4][CH2:3]1.[CH3:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=1[NH:24][CH2:25][CH2:26][NH2:27]>>[CH2:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:1][CH:2]([OH:4])[CH2:3][NH:27][CH2:26][CH2:25][NH:24][C:18]2[C:19]([CH3:23])=[CH:20][CH:21]=[CH:22][C:17]=2[CH3:16])=[CH:7][CH:8]=1)[CH2:14][CH3:15]

Participants

3

Reactant 2

HCID 12666312N-(2,6-dimethylphenyl)-ethylenediamineHCID 202377994-Propoxyphenyl glycidyl ether

Product 1

HCID 128188691-(4-Propoxyphenoxy)-3-[2-(2,6-dimethylphenylamino)-ethylamino]-propan-2-ol

Procedure

4.15 g. 4-Propoxyphenyl glycidyl ether and 6.6 g. N-(2,6-dimethylphenyl)-ethylenediamine are left to stand for 3 days at ambient temperature and the reaction mixture then separated by ion exchange chromatography in the manner described in Example 5. There are obtained 4.3 g. (58% of theory) of the desired product in the form of colorless crystals; m.p. 51°-54° C. The corresponding neutral fumarate, after recrystallization from ethanol, melts at 168°-169° C.

Workup

  1. customthe reaction mixture then separated by ion exchange chromatography in the manner
  2. customThere are obtained 4.3 g

Sources & evidence

ORD record
ord-1231c3b0bcdd4d03a036872d3201cd60
Source dataset
uspto-grants-1986_08
Patent number
US04608383

Reaction notes

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