alpha-(Bromomethyl)benzyl alcohol → alpha-[N-[2-(3-Carbamoyl-4-hydroxy-phenoxy)-ethyl]aminomethyl]-benzyl alcohol

HRID 1462374Notes

Reaction equation

HRID 1462374 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[C:9]([C:10]([NH2:12])=[O:11])[C:8]([OH:14])=[CH:7][CH:6]=1.Br[CH2:16][CH:17]([OH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)(O)[O-].[K+]>C(O)C>[C:10]([C:9]1[CH:13]=[C:5]([CH:6]=[CH:7][C:8]=1[OH:14])[O:4][CH2:3][CH2:2][NH:1][CH2:16][CH:17]([OH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:11])[NH2:12]

Participants

5

Reactant 3

HCID 102812alpha-(Bromomethyl)benzyl alcoholHCID 516893Potassium BicarbonateHCID 230496945-(2-Aminoethoxy)-2-hydroxybenzamide

Product 1

HCID 23276135alpha-[N-[2-(3-Carbamoyl-4-hydroxy-phenoxy)-ethyl]aminomethyl]-benzyl alcohol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 21.9 g of 5-(2-aminoethoxy)-salicylamide, 36.0 g of α-(bromomethyl)-benzyl alcohol and 30 g of potassium bicarbonate in 240 ml of ethanol is refluxed for 15 hours, with stirring. The reaction mixture is then cooled and filtered and the filtrate is evaporated. The evaporation residue is partitioned between 300 ml of ethyl acetate and 100 ml of water and the organic phase is separated off, dried over magnesium sulfate and evaporated. The residue is dissolved hot in as little ethanol as possible and made to crystallise, yielding α-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)ethyl]-aminomethyl]-benzyl alcohol with a melting point of 174°-175° (from ethanol).

Workup

  1. temperatureis refluxed for 15 hours
  2. temperatureThe reaction mixture is then cooled
  3. filtrationfiltered
  4. customthe filtrate is evaporated
  5. customThe evaporation residue is partitioned between 300 ml of ethyl acetate and 100 ml of water
  6. customthe organic phase is separated off
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. dissolutionThe residue is dissolved hot in as little ethanol as possible and
  10. customto crystallise

Sources & evidence

ORD record
ord-8fa8f2331979490aa27b3553660851e5
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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