Hydrogen chloride-ethyl acetate → HCID 66993815, compound

HRID 1879760Notes

Reaction equation

HRID 1879760 reaction equation
C([N:8]1[CH2:14][C:13]2[N:15]=[CH:16][C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH:20]3[CH3:24])=[N:18][C:12]=2[O:11][CH2:10][CH2:9]1)C1C=CC=CC=1.C(OCC)(=O)C.[ClH:31]>CO.[OH-].[OH-].[Pd+2]>[ClH:31].[CH3:24][CH:20]1[CH2:21][CH2:22][CH2:23][N:19]1[C:17]1[CH:16]=[N:15][C:13]2[CH2:14][NH:8][CH2:9][CH2:10][O:11][C:12]=2[N:18]=1

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 66993118HCID 66993118, compound

Product 1

HCID 66993815HCID 66993815, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 8-benzyl-3-(2-methylpyrrolidin-1-yl)-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine (0.51 g) in methanol (15 mL) was added 20% Pd(OH)2/C (0.08 g), and the mixture was stirred under a hydrogen atmosphere at 50° C. for 1 hr. The reaction mixture was filtered, and the filtrate was concentrated. To a solution of the obtained crude product in ethyl acetate (15 mL) was added a 4 N hydrogen chloride-ethyl acetate solution (430 μL) and the mixture was stirred for 30 min. The reaction mixture was filtered, and the obtained crystals were purified by recrystallization (methanol-ethyl acetate) to give the title compound (0.30 g, 71%) as a colorless powder.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customTo a solution of the obtained crude product in ethyl acetate (15 mL)
  4. stirringthe mixture was stirred for 30 min
  5. filtrationThe reaction mixture was filtered
  6. customthe obtained crystals were purified by recrystallization (methanol-ethyl acetate)

Sources & evidence

ORD record
ord-61661822059d40d8b3f04e4d0337da00
Source dataset
uspto-grants-2012_11
Patent number
US08318722B2

Reaction notes

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