HCID 20517522, compound → HCID 20517538, compound

HRID 2198881Notes

Reaction equation

HRID 2198881 reaction equation
[CH2:1]([C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16]C)[CH:11]=2)[O:8][CH2:7][CH2:6][N:5]([CH3:9])[CH2:4]1)[CH3:2]>Br>[CH2:1]([C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=2)[O:8][CH2:7][CH2:6][N:5]([CH3:9])[CH2:4]1)[CH3:2]

Participants

3

Reactant 1

HCID 20517522HCID 20517522, compound

Product 1

HCID 20517538HCID 20517538, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

2-Ethyl-2-(3-methoxyphenyl)-4-methylmorpholine (4.0 g, 0.015 mol) was refluxed for 2.5 hour with aqueous 48% hydrobromic acid (50 ml). The residue on evaporation was dissolved in 2 M sodium hydroxide (50 ml) and the non-phenolic material (about 1.0 g) extracted with ether. The aqueous layer was neutralised with solid ammonium chloride and the phenol extracted with ether/chloroform. The residue on removal of the solvents (1.3 g) was dissolved in isopropyl alcohol and treated with 40% aqueous HBr. The residue on evaporation crystallised from isopropyl alcohol as the hydrobromide hemi-isopropanolate of the title compound (1.24 g, m.p. 99°-104° C.).

Workup

  1. customThe residue on evaporation
  2. dissolutionwas dissolved in 2 M sodium hydroxide (50 ml)
  3. extractionthe non-phenolic material (about 1.0 g) extracted with ether
  4. extractionthe phenol extracted with ether/chloroform
  5. customThe residue on removal of the solvents (1.3 g)
  6. dissolutionwas dissolved in isopropyl alcohol
  7. additiontreated with 40% aqueous HBr
  8. customThe residue on evaporation
  9. customcrystallised from isopropyl alcohol as the hydrobromide hemi-isopropanolate of the title compound (1.24 g, m.p. 99°-104° C.)

Sources & evidence

ORD record
ord-56cecb69020d4619a2e9735ff3688a6e
Source dataset
uspto-grants-1982_11
Patent number
US04360519

Reaction notes

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