Hydrochloric Acid → (S)-Octahydropyrazino[2,1-C][1,4]oxazine dihydrochloride

HRID 1366414Notes

Reaction equation

HRID 1366414 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 59452873(S)-8-Benzyloctahydropyrazino[2,1-c][1,4]oxazine

Product 1

HCID 66649934(S)-Octahydropyrazino[2,1-C][1,4]oxazine dihydrochlorideYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (9aS)-8-(phenylmethyl)octahydropyrazino[2,1-c][1,4]oxazine (assumed 38.02 g, 163.6 mmol) in MeOH (330 mL) was added 6 N aqueous HCl (55 mL, 330 mmol) and 10% Pd/C (3.80 g). The mixture was hydrogenated overnight, and then filtered through a glass fiber filter. The filter cake was washed with MeOH, and the combined solution was concentrated in vacuo and azeotroped with MeOH (4×150 mL) to provide (9aS)-octahydropyrazino[2,1-c][1,4]oxazine dihydrochloride (34.78 g, 99% yield for 2 steps) as a red oil that solidified under high vacuum. LCMS: (M+H)+: 142.9.

Workup

  1. filtrationfiltered through a glass fiber
  2. filtrationfilter
  3. washThe filter cake was washed with MeOH
  4. concentrationthe combined solution was concentrated in vacuo
  5. customazeotroped with MeOH (4×150 mL)

Sources & evidence

ORD record
ord-fc43839b927144db968cd95476683d37
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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