N,N-Dimethylaniline → HCID 15229768, compound

HRID 1609578Notes

Reaction equation

HRID 1609578 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.CN(C)C1C=CC=CC=1.ClC([O:27][C:28](Cl)(Cl)Cl)=O.[C:32]1([CH2:38][CH2:39][CH2:40][CH2:41][NH2:42])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.N1C=CC=CC=1>O1CCCC1.O1CCOCC1>[CH:3]1[C:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[O:6][C:5]=2[CH:13]=[CH:14][C:2]=1[O:1][C:28](=[O:27])[NH:42][CH2:41][CH2:40][CH2:39][CH2:38][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

8

Reactant 5

HCID 949N,N-DimethylanilineHCID 1049PyridineHCID 10426DiphosgeneHCID 665872-DibenzofuranolHCID 83242Benzenebutanamine

Product 1

HCID 15229768HCID 15229768, compoundYield 128.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-hydroxydibenzofuran (5.0 g, 27 mmol) and dimethylaniline (3.4 mL, 27 mmol) in 35 mL of tetrahydrofuran plus 1.5 mL of dioxane was added dropwise under nitrogen to a solution of trichloromethyl chloroformate (1.6 mL, 14 mmol) in 30 mL of tetrahydrofuran at ice bath temperature. After the addition the cooling bath was removed and the stirring continued for approximately 24 hours. The reaction was cooled to ice bath temperature and a solution of 4-phenylbutylamine (4.3 mL, 27 mmol) and pyridine (4.4 mL, 54 mmol) in 30 mL of tetrahydrofuran was added dropwise over 15 minutes. After the addition the reaction was stirred at ice bath temperature for 2 hours. The cooling bath was removed and the stirring continued for approximately 22 hours. The reaction was diluted with ethyl acetate, extracted two times with 1N HCl, dried (MgSO4) and the solvent removed under reduced pressure to give 6.47 g of a yellow solid. Purification of the solid by chromatography on silica gel (230-400 mesh) using hexane-methylene chloride as the eluent gave 1.28 g (13%) of the title compound as a white crystalline solid, mp 113°-114° C.

Workup

  1. additionAfter the addition the cooling bath
  2. customwas removed
  3. temperatureThe reaction was cooled to ice bath temperature
  4. additionAfter the addition the reaction
  5. customThe cooling bath was removed
  6. waitthe stirring continued for approximately 22 hours
  7. additionThe reaction was diluted with ethyl acetate
  8. extractionextracted two times with 1N HCl
  9. dry with materialdried (MgSO4)
  10. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b25bfc783e334fd3a5e64e7f9ea51c4a
Source dataset
uspto-grants-1995_03
Patent number
US05401769

Reaction notes

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