Dichloromethane → N-(2,3-Dihydro-1H-phenalen-2-YL)cyclobutylcarboxamide

HRID 1457934

Reaktionsgleichung

Reaktionsgleichung von HRID 1457934
CO[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7](OC)=[CH:8][CH:9]=2)[CH:4]=1.CC[N:17]([CH2:20][CH3:21])CC.[CH:22]1([C:26](Cl)=[O:27])[CH2:25][CH2:24][CH2:23]1.[CH2:29](Cl)Cl>>[CH2:29]1[C:6]2=[C:5]3[C:10](=[CH:9][CH:8]=[CH:7]2)[CH:11]=[CH:12][CH:3]=[C:4]3[CH2:21][CH:20]1[NH:17][C:26]([CH:22]1[CH2:25][CH2:24][CH2:23]1)=[O:27]

Komponenten

5

Edukt 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 770212,7-DimethoxynaphthaleneHCID 78705Cyclobutanecarbonyl chloride

Produkt 1

HCID 22101284N-(2,3-Dihydro-1H-phenalen-2-YL)cyclobutylcarboxamideAusbeute 40 %

Versuchsvorschrift

To a solution of the amine from Preparation 2 (2 mmol, 350 mg) in 7 cm3 of anhydrous CH2Cl2 in the presence of Et3N (0.4 cm3 ; 1.5 eq.) is added, at 0° C., cyclobutylcarboxylic acid chloride (2 mmol; 0.24 cm3). Stirring is maintained for 1 h at room temperature and the medium is then washed twice with water. The organic phase is dried over MgSO4 and then evaporated. The residue is purified by chromatography on a column of silica gel (particle size 60-200 μm); eluent CH2Cl2 :MeOH 99:1. The expected compound is isolated and recrystallized from a CH2Cl2 :petroleum ether mixture to give 200 mg of the pure expected amide.

Aufarbeitung

  1. additionis added, at 0° C.
  2. washthe medium is then washed twice with water
  3. dry with materialThe organic phase is dried over MgSO4
  4. customevaporated
  5. customThe residue is purified by chromatography on a column of silica gel (particle size 60-200 μm)

Quellen und Nachweise

ORD-Eintrag
ord-7b9d045a6aa246efba098bfe940c01a2
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05849781

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