Methanol → HCID 21519202, compound

HRID 1282999Notes

Reaction equation

HRID 1282999 reaction equation
[OH2:1].Cl.Cl.C([N:11]1[CH2:16][CH2:15][O:14][CH:13]([CH2:17][NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)[CH2:12]1)C1C=CC=CC=1.[H][H].[OH-:29].[Na+].C[OH:32]>[Pd]>[C:21]([OH:25])(=[O:32])[C:22]([OH:29])=[O:1].[CH3:26][O:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[NH:18][CH2:17][CH:13]1[O:14][CH2:15][CH2:16][NH:11][CH2:12]1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 21519213HCID 21519213, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21519202HCID 21519202, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 4-benzyl-2-(3-methoxyanilino)methylmorpholine dihydrochloride monohydrate (2.0 g.) in methanol (50 ml.) is shaken in an atmosphere of hydrogen in the presence of 5% palladium/carbon catalyst until a molar equivalent of hydrogen has been absorbed. The solution is filtered, the methanol evaporated and the residue dissolved in water and the solution thus obtained is basified with dilute sodium hydroxide solution. The mixture is extracted with ether (3 × 100 ml.) and the ethereal solution is dried (MgSO4), filtered and treated with an ethereal solution of oxalic acid. The precipitated oxalate is recrystallised from acetone to give 2-(3-methoxyanilino)methylmorpholine oxalate, m.p. 137°C.

Workup

  1. customhas been absorbed
  2. filtrationThe solution is filtered
  3. customthe methanol evaporated
  4. dissolutionthe residue dissolved in water
  5. customthe solution thus obtained
  6. extractionThe mixture is extracted with ether (3 × 100 ml.)
  7. dry with materialthe ethereal solution is dried (MgSO4)
  8. filtrationfiltered
  9. additiontreated with an ethereal solution of oxalic acid
  10. customThe precipitated oxalate is recrystallised from acetone

Sources & evidence

ORD record
ord-c4546c7b60ac4a8b98e3225eaa0b7e8f
Source dataset
uspto-grants-1976_08
Patent number
US03974156

Reaction notes

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