N,N-Dimethylaniline → HCID 19776529, compound

HRID 1612652Notes

Reaction equation

HRID 1612652 reaction equation
Cl[C:2]([O:4][C:5](Cl)(Cl)Cl)=[O:3].[C:9]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2O)[CH:14]=[CH:13][CH:12]=[CH:11]C=1.CN(C)C1C=CC=CC=1.[CH3:31][CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>C1C=CC=CC=1>[C:9]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[O:4][C:2]([N:35]1[CH2:36][CH2:37][CH:32]([CH3:31])[CH2:33][CH2:34]1)=[O:3]

Participants

6

Reactant 4

HCID 949N,N-Dimethylaniline2×HCID 7017(1,1'-Biphenyl)-2-olHCID 10426DiphosgeneHCID 693814-Methylpiperidine

Product 1

HCID 19776529HCID 19776529, compoundYield 124.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Trichloromethyl chloroformate (3.54 mL, 29.4 mmol) is added dropwise under a nitrogen atmosphere to a solution of 2-phenylphenol (10.0 g, 58.8 mmol) in 150 mL of benzene at room temperature. After the addition, dimethylaniline (7.45 mL, 58.8 mmol) is added dropwise at such a rate that the temperature of the reaction mixture is maintained between 20°-25° C. The resulting mixture is stirred at room temperature for 3 hours. A solution of 4-methylpiperidine (6.95 mL, 58.8 mmol) and dimethylaniline (7.45 mL, 58.8 mmol) in 50 mL of benzene is then added dropwise. After the addition the reaction is stirred at room temperature overnight. The reaction mixture is washed with 1N HCl, 5% NaHCO3, dried (MgSO4) and the solvent removed under reduced pressure. Purification of the crude reaction product by HPLC (hexane-methylene chloride) followed by recrystallization from diisopropyl ether gives the title compound as a white crystalline solid (10.8 g, 62), mp 85° -86° C.

Workup

  1. additionis added dropwise at such a rate that the temperature of the reaction mixture
  2. temperatureis maintained between 20°-25° C
  3. additionAfter the addition the reaction
  4. stirringis stirred at room temperature overnight
  5. washThe reaction mixture is washed with 1N HCl, 5% NaHCO3
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed under reduced pressure
  8. customPurification of the crude
  9. customreaction product by HPLC (hexane-methylene chloride)
  10. customfollowed by recrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-3f4ff06bdac047e788493c851a10eb06
Source dataset
uspto-grants-1993_03
Patent number
US05190940

Reaction notes

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