8-Benzyl-3-(morpholin-4-yl)-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine → 3-(Morpholin-4-yl)-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine

HRID 2188701Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 8-benzyl-3-(morpholin-4-yl)-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine (259 mg), 20% Pd(OH)2/C (300 mg) and methanol (2 mL) was stirred under a hydrogen atmosphere at 50° C. for 2 hr. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (solvent gradient; 0→10% methanol/ethyl acetate) and recrystallized (ethyl acetate-hexane) to give the title compound (54.1 mg, 29%) as colorless crystals.

Workup

filtrationInsoluble material was filtered off
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by basic silica gel column chromatography (solvent gradient; 0→10% methanol/ethyl acetate)
customrecrystallized (ethyl acetate-hexane)

Sources & evidence

ORD record: ord-8d34d150e99b47febdb451eaa167baa5
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324201B2

Reaction notes

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