4-Hydroxybiphenyl → HCID 803546, compound

HRID 1250463Notes

Reaction equation

HRID 1250463 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl[CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.C(=O)([O-])[O-:23].[K+].[K+]>CN(C)C=O>[C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([O:23][CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:3][CH:2]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 71034-HydroxybiphenylHCID 11430Potassium CarbonateHCID 816691-(2-Chloroethyl)pyrrolidine

Product 1

HCID 803546HCID 803546, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

1.76 mol of 4-hydroxybiphenyl, 2.29 mol of 1-(2-chloroethyl)pyrrolidine and 5.3 mol of potassium carbonate are placed in 2.5 liters of dimethylformamide. The whole is heated at 50° C. ovemright. After cooling, the solid is filtered off and the solvent is removed by evaporation. The residue is taken up in ethyl acetate. After washing of the organic phase drying and evaporation, a residue is obtained which is purified by chromatography over silica using an ethyl acetate/ethanol mixture (80/20) as eluant. The expected product is obtained after crystallisation of the residual oil.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid is filtered off
  3. customthe solvent is removed by evaporation
  4. washAfter washing of the organic phase
  5. customdrying
  6. customevaporation
  7. customa residue is obtained which
  8. customis purified by chromatography over silica using an ethyl acetate/ethanol mixture (80/20) as eluant

Sources & evidence

ORD record
ord-f8639d41aa56444a9d4d80a32c962af0
Source dataset
uspto-grants-2002_01
Patent number
US06339092B1

Reaction notes

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