Ethyl Bromide → Ethyl 4-[N-ethyl-(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate

HRID 1097379Notes

Reaction equation

HRID 1097379 reaction equation
[H-].[Na+].[CH:3]1[C:14]2=[C:15]3[CH:10]([CH2:11][CH2:12][CH2:13]2)[CH2:9][CH2:8][CH2:7][C:6]3=[CH:5][C:4]=1[NH:16][C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1.Br[CH2:29][CH3:30].[Cl-].[NH4+]>CN(C)C=O>[CH2:29]([N:16]([C:4]1[CH:3]=[C:14]2[C:15]3[CH:10]([CH2:11][CH2:12][CH2:13]2)[CH2:9][CH2:8][CH2:7][C:6]=3[CH:5]=1)[C:17]1[CH:18]=[CH:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][CH:27]=1)[CH3:30]

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 66811225Ethyl 4-[(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate

Product 1

HCID 58526554Ethyl 4-[N-ethyl-(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoateYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of sodium hydride (60%, 0.009 g) in N,N-dimethylformamide (2 ml) was added with ethyl 4-[(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate (0.037 g) dissolved in N,N-dimethylformamide (1 ml), and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was added with bromoethane (0.02 ml), the mixture was stirred at room temperature for 2 hours, and then added with saturated aqueous ammonium chloride, and the mixture was extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:50) to obtain the title compound (0.036 g, yield: 90%).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:50)

Sources & evidence

ORD record
ord-03c7afa1dc814614b870528e038a9d92
Source dataset
uspto-grants-2012_03
Patent number
US08143260B2

Reaction notes

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