HCID 20517508, compound → HCID 20517513, compound

HRID 2198886Notes

Reaction equation

HRID 2198886 reaction equation
Cl.C[O:3][C:4]1[CH:5]=[C:6]([C:10]2([CH3:18])[O:15][CH:14]([CH3:16])[CH2:13][N:12]([CH3:17])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1>C1(C)C=CC=CC=1>[OH:3][C:4]1[CH:5]=[C:6]([C:10]2([CH3:18])[O:15][CH:14]([CH3:16])[CH2:13][N:12]([CH3:17])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 20517508HCID 20517508, compound

Product 1

HCID 20517513HCID 20517513, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(3-methoxyphenyl)-2,4,6-trimethylmorpholine hydrochloride (Isomer B) (2.49 g) was heated under reflux with redistilled constant boiling hydrobromic acid (20 ml) under nitrogen for 1 hour. After cooling and diluting with water to 40 ml the mixture was basified with conc. aqueous ammonia. The oil which precipitated was extracted with dichloromethane. After drying (MgSO4) the solvent was removed affording a colourless oil which gave 1.16 g of colourless rhombs mp 142°-143° C. from toluene. (Found: C, 70.6; H, 8.7; N, 6.05%. C13H19NO2 requires C, 70.55; H, 8.65; N, 6.3%. NMR data indicate that the product apparently has (2R*, 6S*)-configuration.

Workup

  1. temperatureunder reflux
  2. distillationwith redistilled constant
  3. customfor 1 hour
  4. temperatureAfter cooling
  5. additiondiluting with water to 40 ml the mixture
  6. customThe oil which precipitated
  7. extractionwas extracted with dichloromethane
  8. dry with materialAfter drying (MgSO4) the solvent
  9. customwas removed
  10. customaffording a colourless oil which

Sources & evidence

ORD record
ord-ef1553793b7f48a3889160806fcc7749
Source dataset
uspto-grants-1982_11
Patent number
US04360519

Reaction notes

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