Ethylenediamine → HCID 2990663, compound

HRID 911294Notes

Reaction equation

HRID 911294 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:7])=[C:4]([F:17])[CH:3]=1.[Cu](C#N)[C:19]#[N:20].C(N)CN>CN(C=O)C>[C:19]([C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:7])=[C:4]([F:17])[CH:3]=1)#[N:20]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 90711954-Bromo-N-cyclohexyl-2-fluorobenzamideHCID 178418260HCID 178418260, compound

Product 1

HCID 2990663HCID 2990663, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Heat a mixture of 4-bromo-N-cyclohexyl-2-fluoro-benzamide (1.24 g, 4.13 mmol) and copper cyanide (740 mg, 8.26 mmol) in DMF (20 mL) to reflux for 16 h. Cool the mixture to ambient temperature, add aqueous ethylenediamine and stir for 30 min. Extract the mixture with hexane/EtOAc (1:1), dry the organic layer over Na2SO4, filter and concentrate in vacuo. Purify the residue by chromatography on silica gel eluting with hexane/EtOAc (5:1) to give the desired intermediate as a white solid (620 mg, 61%). MS (ES−) m/z: 245 (M−H)−.

Workup

  1. temperatureHeat
  2. temperatureto reflux for 16 h
  3. extractionExtract the mixture with hexane/EtOAc (1:1)
  4. dry with materialdry the organic layer over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify the residue by chromatography on silica gel eluting with hexane/EtOAc (5:1)

Sources & evidence

ORD record
ord-e1850e6bbbc04e72b25e917297cdd054
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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