Hydrogen chloride-ethyl acetate → (6r)-6-(Methoxymethyl)-n-methyl-n-(1-methylethyl)-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepin-3-amine hydrochloride

HRID 518117Notes

Reaction equation

C([N:8]1[CH2:14][C:13]2[N:15]=[CH:16][C:17]([N:19]([CH3:23])[CH:20]([CH3:22])[CH3:21])=[N:18][C:12]=2[O:11][C@@H:10]([CH2:24][O:25][CH3:26])[CH2:9]1)C1C=CC=CC=1.C(OCC)(=O)C.[ClH:33]>CO.[OH-].[OH-].[Pd+2]>[ClH:33].[CH3:26][O:25][CH2:24][C@H:10]1[CH2:9][NH:8][CH2:14][C:13]2[N:15]=[CH:16][C:17]([N:19]([CH3:23])[CH:20]([CH3:21])[CH3:22])=[N:18][C:12]=2[O:11]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (6R)-8-benzyl-6-(methoxymethyl)-N-methyl-N-(1-methylethyl)-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepin-3-amine (261 mg) in methanol (7 mL) was added 20% Pd(OH)2/C (40 mg), and the mixture was stirred under a hydrogen atmosphere at 50° C. for 7 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. To a solution of the obtained crude product in ethyl acetate (10 mL) was added a 4 N hydrogen chloride-ethyl acetate solution (200 μL), and the mixture was stirred for 30 min. The reaction mixture was filtered, and the obtained crystals were washed with ethyl acetate to give the title compound (136 mg, 61%).

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure
customTo a solution of the obtained crude product in ethyl acetate (10 mL)
stirringthe mixture was stirred for 30 min
filtrationThe reaction mixture was filtered
washthe obtained crystals were washed with ethyl acetate

Sources & evidence

ORD record: ord-5ab4c71a4448499a98ee9b794c32e3a0
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115139B2

Reaction notes

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