Hydrogen chloride-ethyl acetate → N-methyl-N-propyl-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepin-3-amine hydrochloride

HRID 1879765Notes

Reaction equation

C([N:8]1[CH2:14][C:13]2[N:15]=[CH:16][C:17]([N:19]([CH3:23])[CH2:20][CH2:21][CH3:22])=[N:18][C:12]=2[O:11][CH2:10][CH2:9]1)C1C=CC=CC=1.C(OCC)(=O)C.[ClH:30]>CO.[OH-].[OH-].[Pd+2]>[ClH:30].[CH3:23][N:19]([CH2:20][CH2:21][CH3:22])[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

Conditions

Temperature: 50 °C

Procedure

To a solution of 8-benzyl-N-methyl-N-propyl-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepin-3-amine (50 mg) in methanol (4 mL) was added 20% Pd(OH)2/C (10 mg), and the mixture was stirred under a hydrogen atmosphere at 50° C. for 2 hr. The reaction mixture was filtered, and the filtrate was concentrated. To a solution of the obtained crude product in ethyl acetate (2 mL) was added a 4 N hydrogen chloride-ethyl acetate solution (44 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 (27 mg, 65%) as a colorless powder.

Workup

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

Sources & evidence

ORD record: ord-f0667fdcd4e741048654bdb76efab53d
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318722B2

Reaction notes

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