Hydrogen chloride-ethyl acetate → HCID 66993897, compound

HRID 2188705Notes

Reaction equation

HRID 2188705 reaction equation
C([N:8]1[CH2:14][C:13]2[N:15]=[CH:16][C:17]([N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]3[CH3:25])=[N:18][C:12]=2[O:11][CH2:10][CH2:9]1)C1C=CC=CC=1.C(OCC)(=O)C.[ClH:32]>CO.[OH-].[OH-].[Pd+2]>[ClH:32].[CH3:25][CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][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 66993345HCID 66993345, compound

Product 1

HCID 66993897HCID 66993897, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 8-benzyl-3-(2-methylpiperidin-1-yl)-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine (0.65 g) in methanol (20 mL) was added 20% Pd(OH)2/C (0.13 g), 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 (20 mL) was added a 4 N hydrogen chloride-ethyl acetate solution (628 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 (0.40 g, 73%) as a pale-yellow 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 (20 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-59039b121b144c57b33448acbd7bc238
Source dataset
uspto-grants-2012_12
Patent number
US08324201B2

Reaction notes

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