Ethylenediamine → HCID 21841001, compound

HRID 1739491Notes

Reaction equation

HRID 1739491 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][C:10]=1[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([Cu])#[N:25].C(N)CN>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:24]#[N:25])=[CH:11][C:10]=1[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 21840939HCID 21840939, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 21841001HCID 21841001, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of the 4-benzyloxy-3-(phenethyl)phenylbromide, (5.5 g, 15 mmol) in DMF (200 ml, dried) was added CuCN (3.32 g, 37 mmol). The reaction was heated to reflux and held at reflux for 20 hours, under argon. The reaction mixture was allowed to cool to ambient temperature, poured into ice water, treated with ethylene diamine (200 ml) and extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with brine (2×60 ml), dried (MgSO4) and evaporated. The crude material was purified by chromatography to give 4-benzyloxy-3-phenethylbenzonitrile as a white solid (2.0 g, 43%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. temperatureat reflux for 20 hours, under argon
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. washThe combined organic extracts were washed with brine (2×60 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe crude material was purified by chromatography

Sources & evidence

ORD record
ord-e874516f5ee44b55bd3f17dd392301da
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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