2-(4-Methoxyphenoxy)ethylamine → 2-{2-Hydroxy-3-[2-(4-methoxyphenoxy)ethylamino]-propoxy}-5-(2-methoxyethoxy)benzonitrile

HRID 1195081Notes

Reaction equation

HRID 1195081 reaction equation
[O:1]1[CH2:18][CH:2]1[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:9][C:6]=1[C:7]#[N:8].[CH3:19][O:20][C:21]1[CH:30]=[CH:29][C:24]([O:25][CH2:26][CH2:27][NH2:28])=[CH:23][CH:22]=1>C(O)C>[OH:1][CH:2]([CH2:18][NH:28][CH2:27][CH2:26][O:25][C:24]1[CH:29]=[CH:30][C:21]([O:20][CH3:19])=[CH:22][CH:23]=1)[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:9][C:6]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 17977932-(4-Methoxyphenoxy)ethylamineHCID 13313566HCID 13313566, compound

Product 1

HCID 133135672-{2-Hydroxy-3-[2-(4-methoxyphenoxy)ethylamino]-propoxy}-5-(2-methoxyethoxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.4 g of 2-(2,3-epoxypropoxy)-5-(2-methoxyethoxy)-benzonitrile and 8.35 g of 2-(4-methoxyphenoxy)ethylamine are dissolved in 30 ml of ethanol, the solvent is then evaporated and the resulting mixture stirred for 1 hour at 70°. The reaction melt is then dissolved in ether and allowed to crystallize under cooling. Purification is effected by recrystallization in benzene. The title compound is obtained (M.P. 95°-97°).

Workup

  1. customthe solvent is then evaporated
  2. dissolutionThe reaction melt is then dissolved in ether
  3. customto crystallize
  4. temperatureunder cooling
  5. customPurification
  6. customis effected by recrystallization in benzene

Sources & evidence

ORD record
ord-472781582779427499382d0354e23d27
Source dataset
uspto-grants-1989_03
Patent number
US04816604

Reaction notes

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