HCID 20517506, compound → HCID 20517553, compound

HRID 2198890Notes

Reaction equation

HRID 2198890 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][CH:7]([CH3:9])[CH2:6][NH:5][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][CH:7]([CH3:9])[CH2:6][NH:5][CH2:4]1)[CH3:2]

Participants

3

Reactant 1

HCID 20517506HCID 20517506, compound

Product 1

HCID 20517553HCID 20517553, compoundYield 113.2%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

2-Ethyl-2-(3-methoxyphenyl)-6-methylmorpholine (2.63 g) was refluxed with aq 48% HBr (20 ml) for 2.5 h. The residue on evaporation was re-evaporated from isopropyl alcohol several times, giving ultimately a green gum (2.8 g), which was dissolved in methanol and basified with 0.880 ammonia. The methanol and ammonia were evaporated under reduced pressure and the aqueous remaining was shaken with chloroform (2×100 ml). The chloroform layers were washed and dried and evaporated, leaving an orange oil (8.4 g) that crystallised from ethyl acetate (25 ml). The yellow hygroscopic solid was dissolved in isopropyl alcohol (15 ml) and acidified with ethereal hydrogen chloride. On cooling crystals of the title compound hydrochloride were obtained (0.85 g, mp 200°-205° C.). Gas-liquid chromatography revealed the isomer ratio to be 20:1.

Workup

  1. customThe residue on evaporation
  2. customwas re-evaporated from isopropyl alcohol several times

Sources & evidence

ORD record
ord-fc64a721cf4d4f86a2719c32c15f668f
Source dataset
uspto-grants-1982_11
Patent number
US04360519

Reaction notes

Loading…