Benzyloxyamine hydrochloride → HCID 178419047, compound

HRID 1370309

Reaction equation

HRID 1370309 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

4

Reactant 2

HCID 102312Benzyloxyamine hydrochlorideHCID 219862665'-Bromo-2'-(methylthio)spiro[cyclohexane-1,3'-[3H]indole]

Product 1

HCID 178419047HCID 178419047, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 (9:1 Hexane/EtOAc) to the desired product (6.5 g, 60%). 1H NMR (DMSO-d6, 300 MHz) δ 1.38-1.70 (m, 8H), 1.92-2.06 (m, 2H), 5.06 (s, 2H), 6.71 (d, 1H, J=8.26 Hz), 7.22-7.43 (m, 7H), 9.62 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-5098e9b124f94145ba6c2c6f2032b172
Source dataset
uspto-grants-2003_06
Patent number
US06583145B1

Linked notes

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