Benzylamine → HCID 57431197, compound

HRID 2377619Notes

Reaction equation

HRID 2377619 reaction equation
C[C:2]1[C:3]([O:13][CH3:14])=[C:4]([CH2:11]Br)[C:5]([CH2:9]Br)=[C:6]([Br:8])[CH:7]=1.BrC1C=CC(OC)=C(C)C=1C.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CC#N>[CH2:26]([N:33]1[CH2:9][C:5]2[C:4](=[C:3]([O:13][CH3:14])[CH:2]=[CH:7][C:6]=2[Br:8])[CH2:11]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 27525994-Bromo-2,3-dimethylanisoleHCID 86610194HCID 86610194, compound

Product 1

HCID 57431197HCID 57431197, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 1-bromo-2,3-bis(bromomethyl)-4-methoxybenzene (prepared as described in J. Org. Chem. 1992, 57, 6374, from commercially available 1-bromo-4-methoxy-2,3-dimethylbenzene) in CH3CN (0.1 M) were added 2.5 eq of KHCO3 and the mixture heated at 60° C. Then 1 eq. of benzylamine in CH3CN (0.9 M) was added within 15 minutes and the mixture was heated to reflux for 2 h. The reaction mixture was allowed to cool, filtered over celite and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel (5% EtOAc in petroleum ether, then 10%) to afford the title compound (55%). 1H NMR (300 MHz, CDCl3, ppm) δ 3.77 (s, 3H), 3.92 (s, 2H), 3.98 (s, 2H), 4.01 (s, 2H), 6.60 (d, J 8.6, 1H), and 7.22-7.46 (m, 6H). MS (ES+) m/z 318, 320 (M+H)+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h
  3. temperatureto cool
  4. filtrationfiltered over celite and
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography on silica gel (5% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-21c0bb6665fb405f80573a79590679ec
Source dataset
uspto-grants-2008_12
Patent number
US07470664B2

Reaction notes

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