Hydrochloric Acid → Methyl 5-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenoxy]furan-2-carboxylate, hydrochloride

HRID 465433Notes

Reaction equation

HRID 465433 reaction equation
[CH2:1]([C:5]1[CH:20]=[CH:19][C:8]([O:9][C:10]2[O:14][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)[C:2]([CH3:4])=O.[OH:21][CH:22]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=1)[CH2:23][NH2:24].O.Cl>C1C=CC=CC=1>[ClH:31].[Cl:31][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[CH:22]([OH:21])[CH2:23][NH:24][CH:2]([CH3:4])[CH2:1][C:5]1[CH:20]=[CH:19][C:8]([O:9][C:10]2[O:14][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 19874529HCID 19874529, compound

Product 1

HCID 131717569Methyl 5-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenoxy]furan-2-carboxylate, hydrochloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of methyl 5-[4-acetonylphenoxy]furan-2-carboxylate (1.04 g) and 2-hydroxy-2-(3-chlorophenyl)ethanamine (0.65 ) in dry benzene (100 ml) was heated under reflux, with azeotropic removal of water, for 1 hr. the solvent was evaporated and the residue dissolved in methanol (100 ml), cooled, and treated with sodium borohydride (0.4 g), in portions. The reaction mixture was stirred at ambient temperature for 2 hr. The solvent was evaporated and the residue partitioned between water and chloroform. The organic layer was dried (MgSO4) and evaporated to an oil which was purified by column chromatography on silica gel. Elution with 4% methanol:chloroform gave a colourless oil. An ethereal solution of the free base was treated with hydrogen chloride gas to give methyl 5-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxy]furan-2-carboxylate, hydrochloride as a 65:35 mixture of diastereoisomers, m.p. 148°-150° C. (ethylacetate-ether).

Workup

  1. temperaturewas heated
  2. customthe solvent was evaporated
  3. dissolutionthe residue dissolved in methanol (100 ml)
  4. temperaturecooled
  5. additiontreated with sodium borohydride (0.4 g), in portions
  6. customThe solvent was evaporated
  7. customthe residue partitioned between water and chloroform
  8. dry with materialThe organic layer was dried (MgSO4)
  9. customevaporated to an oil which
  10. customwas purified by column chromatography on silica gel
  11. washElution with 4% methanol
  12. customchloroform gave a colourless oil

Sources & evidence

ORD record
ord-85c7f4af58ee42649a00df796f466464
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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