1-(Biphenyl-4-yloxy)-2,3-epoxypropane → 1-[N-benzyl-2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-(4-biphenyloxy)-2-propanol

HRID 638037Notes

Reaction equation

HRID 638037 reaction equation
[O:1]1[CH2:17][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.[CH2:18]([NH:25][CH2:26][CH2:27][O:28][C:29]1[CH:37]=[C:33]([C:34]([NH2:36])=[O:35])[C:32]([OH:38])=[CH:31][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)(C)C>[CH2:18]([N:25]([CH2:26][CH2:27][O:28][C:29]1[CH:30]=[CH:31][C:32]([OH:38])=[C:33]([C:34](=[O:35])[NH2:36])[CH:37]=1)[CH2:17][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 1073251-(Biphenyl-4-yloxy)-2,3-epoxypropaneHCID 137544195-[2-(Benzylamino)-ethoxy]-salicylamide

Product 1

HCID 202551611-[N-benzyl-2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-(4-biphenyloxy)-2-propanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 5.97 g of 4-(2,3-epoxypropoxy)-biphenyl and 6.87 g of 5-[2-(benzylamino)-ethoxy]-salicylamide in 140 ml of isopropanol is heated under reflux for 15 hours and the solvent is then removed in a rotary evaporator. The residue is recrystallised from diethyl ether, yielding 1-[N-benzyl-2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-(4-biphenyloxy)-2-propanol having a melting point of 135°-138°.

Workup

  1. temperatureunder reflux for 15 hours
  2. customthe solvent is then removed in a rotary evaporator
  3. customThe residue is recrystallised from diethyl ether

Sources & evidence

ORD record
ord-3dce6523b40644ecb789251b56f6870c
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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