Sodium Hydroxide → HCID 86733814, compound

HRID 1283112Notes

Reaction equation

HRID 1283112 reaction equation
[ClH:1].Cl.C([N:10]1[CH2:15][CH2:14][O:13][C@@H:12]([CH2:16][NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH2:25][CH3:26])[CH2:11]1)C1C=CC=CC=1.[H][H].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[OH-].[Na+]>C(O)C.O.[Pd]>[ClH:1].[CH2:25]([O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH:17][CH2:16][C@H:12]1[O:13][CH2:14][CH2:15][NH:10][CH2:11]1)[CH3:26]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 86733816HCID 86733816, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 86733814HCID 86733814, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of (2S)-4-benzyl-2-(2-ethoxyanilino)methylmorpholine dihydrochloride (5 g.) in a mixture of ethanol (50 ml.) and water (5 ml.) is shaken in an atmosphere of hydrogen with palladium on carbon catalyst (0.5 g. 5%) until no more hydrogen is absorbed. The catalyst is removed by filtration and the filtrate is evaporated under reduced pressure when (2S)-2-(2-ethoxyanilino)methylmorpholine dihydrochloride (3.7 g.) is obtained as a hydroscopic solid. The dihydrochloride is dissolved in water (100 ml.), the solution is basified with sodium hydroxide solution and extracted with ether (2 × 100 ml.). The ethereal extract is dried (Na2SO4), filtered and the filtrate is then carefully titrated with an ethereal solution of hydrogen chlroide to give (2S)-2-(2-ethoxyanilino)methylmorpholine hydrochloride, m.p. 158°-159°C. on recrystallisation from ethanol [α]D28 - 2.2° (c,4 in methanol).

Workup

  1. customis absorbed
  2. customThe catalyst is removed by filtration
  3. customthe filtrate is evaporated under reduced pressure when (2S)-2-(2-ethoxyanilino)methylmorpholine dihydrochloride (3.7 g.)
  4. customis obtained as a hydroscopic solid
  5. extractionextracted with ether (2 × 100 ml.)
  6. extractionThe ethereal extract
  7. dry with materialis dried (Na2SO4)
  8. filtrationfiltered

Sources & evidence

ORD record
ord-708c3ebcfe0d403c8cc316966ba1a440
Source dataset
uspto-grants-1976_08
Patent number
US03974158

Reaction notes

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