Benzenemethanol, 4-amino-alpha-(aminomethyl)-3,5-dichloro- → 2-[4-[2-[(4-amino-3,5-dichloro-beta-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one

HRID 465421Notes

Reaction equation

HRID 465421 reaction equation
[CH2:1]([C:5]1[CH:20]=[CH:19][C:8]([O:9][CH2:10][C:11]2[O:12][CH:13]=[C:14]([OH:18])[C:15](=[O:17])[CH:16]=2)=[CH:7][CH:6]=1)[C:2]([CH3:4])=O.[NH2:21][C:22]1[C:27]([Cl:28])=[CH:26][C:25]([CH:29]([OH:32])[CH2:30][NH2:31])=[CH:24][C:23]=1[Cl:33]>C1C=CC=CC=1>[NH2:21][C:22]1[C:23]([Cl:33])=[CH:24][C:25]([CH:29]([OH:32])[CH2:30][NH:31][CH:2]([CH3:4])[CH2:1][C:5]2[CH:20]=[CH:19][C:8]([O:9][CH2:10][C:11]3[O:12][CH:13]=[C:14]([OH:18])[C:15](=[O:17])[CH:16]=3)=[CH:7][CH:6]=2)=[CH:26][C:27]=1[Cl:28]

Participants

4

Reactant 2

HCID 217242Benzenemethanol, 4-amino-alpha-(aminomethyl)-3,5-dichloro-HCID 198745552-(4-acetonylphenoxymethyl)-5-hydroxy-4H-pyran-4-one

Product 1

HCID 198745482-[4-[2-[(4-amino-3,5-dichloro-beta-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2-[4-acetonylphenoxymethyl]-5-hydroxy-4H-pyran-4-one (1.0 g) and 2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethylamine (0.75 g) in benzene, was heated to reflux for 3 hours under a Dean and Stark head. After cooling, the solvent was removed in vacuo, the residue dissolved in methanol, treated with sodium cyanoborohydride (0.25 g) and then stirred at ambient temperature for 18 hours. The solvent was evaporated under reduced pressure and the residue taken up in ethyl acetate and washed with water (2×50ml), brine (1×50 ml) and dried (MgSO4). After filtration and evaporation of solvent the residue was purified by column chromatography on silica using 3% methanol:chloroform as eluent to give 2-[4-[2-[(4-amino-3,5-dichloro-β-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one as a (40:60) mixture of diastereoisomers.

Workup

  1. temperatureto reflux for 3 hours under a Dean and Stark head
  2. temperatureAfter cooling
  3. customthe solvent was removed in vacuo
  4. dissolutionthe residue dissolved in methanol
  5. additiontreated with sodium cyanoborohydride (0.25 g)
  6. customThe solvent was evaporated under reduced pressure
  7. washwashed with water (2×50ml), brine (1×50 ml)
  8. dry with materialdried (MgSO4)
  9. filtrationAfter filtration and evaporation of solvent the residue
  10. customwas purified by column chromatography on silica using 3% methanol

Sources & evidence

ORD record
ord-8f3d8ec3edbe411c948926b586bc84d6
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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