Hydrochloric Acid → (R)-Octahydropyrazino[2,1-c][1,4]oxazine dihydrochloride

HRID 1366562Notes

Reaction equation

HRID 1366562 reaction equation
C1(C[N:8]2[CH2:17][CH2:16][N:15]3[C@@H:10]([CH2:11][O:12][CH2:13][CH2:14]3)[CH2:9]2)C=CC=CC=1.[ClH:18]>CO.[Pd]>[ClH:18].[ClH:18].[CH2:11]1[C@H:10]2[CH2:9][NH:8][CH2:17][CH2:16][N:15]2[CH2:14][CH2:13][O:12]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54298313(9aR)-8-(phenylmethyl)octahydropyrazino[2,1-c][1,4]oxazine

Product 1

HCID 66936480(R)-Octahydropyrazino[2,1-c][1,4]oxazine dihydrochlorideYield 103.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (9aR)-8-(phenylmethyl)octahydropyrazino[2,1-c][1,4]oxazine (1.8055 g, 7.77 mmol) in MeOH (80 mL) was added 1 N aq. HCl (15.5 mL, 15.5 mmol) and 10% Pd/C (50% water, 360 mg). The mixture was hydrogenated under balloon pressure overnight, and was then filtered through a 0.2 μm PTFE membrane. The solution was concentrated in vacuo and the residue was azeotroped with MeOH (3×50 mL) to provide crude (9aR)-octahydropyrazino[2,1-c][1,4]oxazine dihydrochloride (1.7185 g, >100% crude yield) as an orange solid. LCMS: (M+H)+: 142.9.

Workup

  1. customwas hydrogenated under balloon pressure overnight
  2. filtrationwas then filtered through a 0.2 μm PTFE membrane
  3. concentrationThe solution was concentrated in vacuo
  4. customthe residue was azeotroped with MeOH (3×50 mL)

Sources & evidence

ORD record
ord-618743275cc849ae8d567d37ad0c1bde
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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