N,N,N',N'-Tetramethylethylenediamine → HCID 18779202, compound

HRID 1422357Notes

Reaction equation

HRID 1422357 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.CN(CCN(C)C)C.C([Li])CCC.C([Cu])#N.[CH:31](N1CCCCC1)=[O:32]>CCOCC>[OH:8][CH2:7][C:4]1[CH:3]=[CH:2][C:1]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]=1[CH:31]=[O:32]

Participants

7

Reactant 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 174291-PiperidinecarboxaldehydeHCID 19186(1,1'-Biphenyl)-4-methanolHCID 178418339ButyllithiumHCID 178418546HCID 178418546, compound

Product 1

HCID 18779202HCID 18779202, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-60 °C

Procedure

To a solution of 4-biphenylmethanol (0.368 g, 2 mmol) in ether (25 mL) and TMEDA (1.21 mL, 8 mmol), at 0° C. was added n-butyllithium (2.5N hexanes; 3.2 mL, 8 mmol). The solution was then heated at reflux for 1 h, cooled to -60° C. and CuCN (0.2 g, 2.2 mmol) added. After 30 minutes, the solution was cooled to -78° C. and N-formylpiperidine (1.11 mL, 10 mmol) was then added dropwise and stirring was continued for 1 h. The mixture was then warmed to -10° C., quenched with saturated NH4Cl, extracted with ether washed with brine, dried and the solvent removed in vacuo. Chromatography of the residue (silica gel; hexane:EtOAc 4:1) afforded the title compound as a colorless oil.

Workup

  1. temperatureThe solution was then heated
  2. temperatureat reflux for 1 h
  3. temperaturethe solution was cooled to -78° C.
  4. waitwas continued for 1 h
  5. temperatureThe mixture was then warmed to -10° C.
  6. customquenched with saturated NH4Cl
  7. extractionextracted with ether
  8. washwashed with brine
  9. customdried
  10. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-32d21387fae64f69a50b41dc5dc52eea
Source dataset
uspto-grants-2000_06
Patent number
US06080870

Reaction notes

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