1-Benzylazepan-2-one → Stk283925

HRID 1484226Notes

Reaction equation

HRID 1484226 reaction equation
C[SiH](C)C1C=CC=CC=1[SiH](C)C.[CH2:13]([N:20]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][C:21]1=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[CH2:13]([N:20]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 14910681-Benzylazepan-2-oneHCID 2733841o-Phenylenebis(dimethylsilane)

Product 1

HCID 10954328Stk283925Yield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A 20-mL eggplant flask equipped with a three-way cock and a magnetic stirrer was heat dried while pumping to a vacuum of 5 Pa before its interior was purged with argon atmosphere. Into the flask, iron complex A (1.0 mg, 0.002 mmol) was admitted as catalyst and dissolved in toluene (0.5 mL). To the solution, 1,2-bis(dimethylsilyl)benzene (475 μL) was added through a syringe, and N-benzyl-ε-caprolactam (203 mg, 1.0 mmol) was added. The solution was stirred at 100° C. for 30 minutes. Toluene was distilled off in vacuum. The crude product was purified by silica gel-packed column chromatography using hexane/ethyl acetate (10/1) as developing solvent, obtaining 1-benzylazepane (169 mg, 0.89 mmol, 89%). The results are shown as Entry 5 in Table 5. The resulting amine was identified for geometry by 1H and 13C-NMR spectroscopy and IR spectroscopy.

Workup

  1. customA 20-mL eggplant flask equipped with a three-way cock and a magnetic stirrer
  2. temperaturewas heat
  3. customdried
  4. customwas purged with argon atmosphere
  5. distillationToluene was distilled off in vacuum
  6. customThe crude product was purified by silica gel-

Sources & evidence

ORD record
ord-0edeb10465374551b8c55a01b1a481c5
Source dataset
uspto-grants-2016_08
Patent number
US09421532B2

Reaction notes

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