Diisopropyl Ether → N-[2-t-Butyl-5-(3-phenyl-3-oxopropyl)phenyl]-2-(9H-xanthen-9-yl)acetamide

HRID 1734871Notes

Reaction equation

HRID 1734871 reaction equation
C(N(CC)CC)C.C(P(Cl)(CC)=O)C.[CH:15]1[C:28]2[CH:27]([CH2:29][C:30](O)=[O:31])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[O:20][C:19]=2[CH:18]=[CH:17][CH:16]=1.[C:33]([C:37]1[CH:43]=[CH:42][C:41]([CH2:44][CH2:45][C:46]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:47])=[CH:40][C:38]=1[NH2:39])([CH3:36])([CH3:35])[CH3:34].C(OC(C)C)(C)C>C(OCC)(=O)C.N1(C2C=CN=CC=2)CCCC1.C1C=CC=CC=1>[C:33]([C:37]1[CH:43]=[CH:42][C:41]([CH2:44][CH2:45][C:46]([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)=[O:47])=[CH:40][C:38]=1[NH:39][C:30](=[O:31])[CH2:29][CH:27]1[C:28]2[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=2[O:20][C:21]2[C:26]1=[CH:25][CH:24]=[CH:23][CH:22]=2)([CH3:36])([CH3:34])[CH3:35]

Participants

9

Reactant 5

HCID 7914Diisopropyl EtherHCID 8471TriethylamineHCID 8346622-(9H-xanthen-9-yl)acetic acidHCID 5195381Diethylphosphinoyl chlorideHCID 199662012-t-Butyl-5-(3-phenyl-3-oxopropyl)aniline

Product 1

HCID 19965997N-[2-t-Butyl-5-(3-phenyl-3-oxopropyl)phenyl]-2-(9H-xanthen-9-yl)acetamideYield 88.7%

Reagents, catalysts & solvents 3

HCID 755674-PyrrolidinopyridineCatalystHCID 241BenzeneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

0.58 ml (4.20 mmol) of triethylamine and 0.31 ml (2.10 mmol) of diethylphosphoryl chloride were added to 20 ml of a benzene suspension containing 505 mg (2.10 mmol) of 2-(9H-xanthen-9-yl)acetic acid, and then the mixture was stirred for 1 hour. At the end of this time, 5 ml of a benzene solution containing 587 mg (2.09 mmol) of 2-t-butyl-5-(3-phenyl-3-oxopropyl)aniline (prepared by a procedure similar to that described in Preparation 7), followed by 10 mg of 4-pyrrolidinopyridine, were added to the reaction suspension, and the resulting mixture was heated under reflux for 4.5 hours. The reaction mixture was then diluted with ethyl acetate, washed with dilute aqueous hydrochloric acid, with water, with a saturated aqueous solution of sodium hydrogen carbonate solution and with a saturated aqueous solution of sodium chloride, in that order. The solvent was then removed by distillation under reduced pressure, and the resulting residue was subjected to column chromatography through silica gel. Elution with a 4:1 by volume mixture of methylene chloride and cyclohexane yielded 934 mg (yield 86%) of the title compound as crystals, melting at 116°-118° C. (after crystallization from diisopropyl ether).

Workup

  1. customprepared by a procedure similar to
  2. customthat described in Preparation 7),
  3. additionwere added to the reaction suspension
  4. temperaturethe resulting mixture was heated
  5. temperatureunder reflux for 4.5 hours
  6. washwashed with dilute aqueous hydrochloric acid, with water, with a saturated aqueous solution of sodium hydrogen carbonate solution and with a saturated aqueous solution of sodium chloride, in that order
  7. customThe solvent was then removed by distillation under reduced pressure
  8. washElution with a 4:1
  9. additionby volume mixture of methylene chloride and cyclohexane
  10. customyielded

Sources & evidence

ORD record
ord-12ced077d6014275855e78d7523f9dad
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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