Hydrogen Bromide → HCID 20517530, compound

HRID 2198893Notes

Reaction equation

HRID 2198893 reaction equation
Cl.[CH2:2]([C:4]1([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[CH:18]=2)[O:9][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:7][N:6]([CH3:16])[CH2:5]1)[CH3:3].Br>>[CH2:2]([C:4]1([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=2)[O:9][CH:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:7][N:6]([CH3:16])[CH2:5]1)[CH3:3]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 20517535HCID 20517535, compound

Product 1

HCID 20517530HCID 20517530, compound

Procedure

2-Ethyl-2-(3-methoxyphenyl)-4-methyl-6-phenylmorpholine hydrochloride (Isomer B from Example 22) (607 mg) was heated under reflux with concentrated hydrobromic acid (5 ml) for 1.25 h. On cooling crystals and a dark gum separated. The hydrobromic acid was removed under reduced pressure and the gummy product re-evaporated with portions of isopropyl alcohol. The product was recrystallised from isopropyl alcohol to give the title compound of apparently 2R*,6S* configuration (422 mg), mp 250°-252° C.

Workup

  1. temperatureOn cooling crystals
  2. customa dark gum separated
  3. customThe hydrobromic acid was removed under reduced pressure
  4. customthe gummy product re-evaporated with portions of isopropyl alcohol
  5. customThe product was recrystallised from isopropyl alcohol

Sources & evidence

ORD record
ord-c01597fa97694f2b85e9995be4f313d4
Source dataset
uspto-grants-1982_11
Patent number
US04360519

Reaction notes

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