N,N-Dimethylaniline → HCID 15225152, compound

HRID 274911Notes

Reaction equation

HRID 274911 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:16]([CH3:23])[C:17]1C=[CH:21][CH:20]=[CH:19][CH:18]=1.ClC(OC(Cl)(Cl)Cl)=[O:26].N1CCCCC1.N1C=CC=CC=1>C1C=CC=CC=1.O1CCOCC1>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][C:23]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:26])=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 949N,N-DimethylanilineHCID 1049PyridineHCID 8082PiperidineHCID 10426DiphosgeneHCID 132544-Phenoxyphenol

Product 1

HCID 15225152HCID 15225152, compoundYield 182.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-phenoxyphenol (5.0 g, 26.9 mmol) and dimethylaniline (3.4 ml, 26.8 mmol) in 35 ml of benzene plus 1.5 ml of dioxane was added dropwise over 15 minutes under a nitrogen atmosphere to a solution of trichloromethyl chloroformate (1.6 ml, 13.3 mmol) in 30 ml of benzene at ice bath temperature. After the addition, the cooling bath was removed and the stirring continued for 24 hours. The reaction was cooled to ice bath temperature and a solution of piperidine (2.7 ml, 27.3 mmol) and pyridine (4.4 ml, 54.4 mmol) in 20 ml of benzene was added dropwise over 15 minutes. After the addition, the reaction was stirred at ice bath temperature for 3 hours. The cooling bath was removed and the stirring continued for 22 hours. The reaction was diluted with benzene and extracted two times with 1 N HCl. The organic solution was dried over anhydrous MgSO4 and the solvent was removed under reduced pressure to give 7.21 g of an oil. Purification by HPLC (hexane:EtOAc) gave 5.05 g of a light yellow crystalline solid. Recrystallization from diisopropyl ether gave the title compound as a white crystalline solid (3.11 g, 39%), mp 74°-76° C.

Workup

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. temperatureThe reaction was cooled to ice bath temperature
  4. additionAfter the addition
  5. customThe cooling bath was removed
  6. waitthe stirring continued for 22 hours
  7. additionThe reaction was diluted with benzene
  8. extractionextracted two times with 1 N HCl
  9. dry with materialThe organic solution was dried over anhydrous MgSO4
  10. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b4180035a55c4307afd5adfd220e842e
Source dataset
uspto-grants-1995_02
Patent number
US05391571

Reaction notes

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