Benzyloxyamine hydrochloride → HCID 178419047, compound

HRID 496685

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]=[C:6](SC)[C:5]12[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.Cl.[CH2:19]([O:26][NH2:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO>[CH2:19]([O:26][N:27]=[C:6]1[C:5]2([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=2)[NH:7]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 45 °C

Procedure

5′-Bromo-2′-(methylthio)spiro[cyclohexane-1,3′-[3H ]indole] (9.0 g, 28.98 mmol) and O-benzylhydroxylamine hydrochloride (13.8 g, 86.9 .mmol) were combined in methanol (150 mL) and heated to 45° C. for 6 hours. Methanol was evaporated in vacuo. Ethyl acetate was added to the residue and this mixture was washed with ammonium chloride solution. Ethyl acetate was dried over magnesium sulfate, ethyl acetate collected evaporated in vacuo and the residue was flash chromatographed on alumina 90 (9:1Hexane/EtOAc) to the desired product (6.5 g, 60%).

Workup

customMethanol was evaporated in vacuo
additionEthyl acetate was added to the residue
washthis mixture was washed with ammonium chloride solution
dry with materialEthyl acetate was dried over magnesium sulfate, ethyl acetate
customcollected
customevaporated in vacuo
customchromatographed on alumina 90 (9:1Hexane/EtOAc) to the desired product (6.5 g, 60%)

Sources & evidence

ORD record: ord-cb1327f5964c4c7fb782c4a801d50834
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06946454B2

Linked notes

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