Potassium Iodide → 1-(2'-Cyano-phenoxy)-2-hydroxy-3-[(2"-methyl-2"-hydroxy-ethyl)-amino]-propane

HRID 1077072Notes

Reaction equation

HRID 1077072 reaction equation
[C:1]([C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[O:5][CH2:6][CH:7]([OH:10])[CH2:8][NH2:9])#[N:2].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].[CH2:23](Cl)[CH:24]([OH:26])[CH3:25]>C(O)C>[C:1]([C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[O:5][CH2:6][CH:7]([OH:10])[CH2:8][NH:9][CH2:23][CH:24]([CH3:25])[OH:26])#[N:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 313701-Chloro-2-propanolHCID 1931632-(3-Amino-2-hydroxypropoxy)benzonitrile

Product 1

HCID 214340881-(2'-Cyano-phenoxy)-2-hydroxy-3-[(2"-methyl-2"-hydroxy-ethyl)-amino]-propane

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture consisting of 0.3 gm (about 0.0015 mol) of 1-(2'-cyano-phenoxy)-2-hydroxy-3-amino-propane, 5 ml of absolute ethanol, 0.21 gm (0.002 mol) of sodium carbonate, 30 mgm of potassium iodide and 0.189 gm (0.002 mol) of propylene chlorohydrin was refluxed for 20 hours, accompanied by stirring. Thereafter, the reaction mixture was worked up in conventional manner, and the isolated raw reaction product was purified by chromatography in a silicagel column, yielding the free base 1-(2'-cyano-phenoxy)-2-hydroxy-3-[(2"-methyl-2"-hydroxy-ethyl)-amino]-propane.

Workup

  1. temperaturewas refluxed for 20 hours
  2. customthe isolated raw
  3. customreaction product
  4. customwas purified by chromatography in a silicagel column

Sources & evidence

ORD record
ord-3570d6e6ea6049cca9ab31db33cd3f44
Source dataset
uspto-grants-1976_05
Patent number
US03959338

Reaction notes

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