Azepane → HCID 10634297, compound

HRID 1929021Notes

Reaction equation

HRID 1929021 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[NH:13]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:10]([C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][N:13]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:5][CH:6]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 8119AzepaneHCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromide

Product 1

HCID 10634297HCID 10634297, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2-Bromo-ethyl)-4-nitro-benzene (10 g, 43.47 mmol) is added under argon to a mixture of azepane (4.9 ml, 43.47 mmol) and potassium carbonate (6 g, 43.47 mmol) in 100 ml of DMF. After stirring over night at room temperature, the mixture is filtered and evaporated under high vacuum. The residue is dissolved in ethyl acetate, washed with water and brine and dried over sodium sulfate. Evaporation gave 9.1 g (84%) of a yellow oil.

Workup

  1. filtrationthe mixture is filtered
  2. customevaporated under high vacuum
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customEvaporation

Sources & evidence

ORD record
ord-b2d8cb329fd14043af94cb058f3d4f84
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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