Hydrogen chloride-ethyl acetate → HCID 66993335, compound

HRID 1877886Notes

Reaction equation

HRID 1877886 reaction equation
C([N:8]1[CH2:14][C:13]2[N:15]=[CH:16][C:17]([N:19]([CH2:21][CH:22]3[CH2:24][CH2:23]3)[CH3:20])=[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].[CH:22]1([CH2:21][N:19]([CH3:20])[C:17]2[CH:16]=[N:15][C:13]3[CH2:14][NH:8][CH2:9][CH2:10][O:11][C:12]=3[N:18]=2)[CH2:23][CH2:24]1

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 66993127HCID 66993127, compound

Product 1

HCID 66993335HCID 66993335, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 8-benzyl-N-(cyclopropylmethyl)-N-methyl-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepin-3-amine (0.36 g) in methanol (10 mL) was added 20% Pd(OH)2/C (70 mg), and the mixture was stirred under a hydrogen atmosphere at 50° C. for 2.5 hr. The reaction mixture was filtered, and the filtrate was concentrated. To a solution of the obtained crude product in ethyl acetate (10 mL) was added a 4 N hydrogen chloride-ethyl acetate solution (300 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 (197 mg, 67%) 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 (10 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-58ea8bb2b13f4bea9cc152ad911d732e
Source dataset
uspto-grants-2012_11
Patent number
US08314088B2

Reaction notes

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