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Water → N-(2,6-Diisopropylphenyl)-2-(2-oxo-1-phenyl-1,3-diazaspiro[4.5]dec-3-yl)-acetamide

HRID 1894852
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1894852
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH:13]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]([CH3:24])[CH3:23])[C:17]=1[NH:25][C:26](=[O:43])[CH2:27][NH:28][CH2:29][C:30]1([NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)([CH3:15])[CH3:14].C(N(C(C)C)CC)(C)C.O>ClCCl>[CH:13]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]([CH3:24])[CH3:23])[C:17]=1[NH:25][C:26](=[O:43])[CH2:27][N:28]1[CH2:29][C:30]2([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]2)[N:36]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:2]1=[O:4])([CH3:14])[CH3:15]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 25227156N-(2,6-diisopropylphenyl)-2-[(1-phenylamino-cyclohexylmethyl)amino]acetamide

Produkt 1

HCID 25226974N-(2,6-Diisopropylphenyl)-2-(2-oxo-1-phenyl-1,3-diazaspiro[4.5]dec-3-yl)-acetamideAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

136 mg (0.46 mmol) of triphosgene are added to 10 ml of dichloro-methane. The medium is cooled to 0° C. and a solution of 580 mg (1.37 mmol) of N-(2,6-diisopropylphenyl)-2-[(1-phenylaminocyclohexyl-methyl)amino]acetamide and 260 μl (1.49 mmol) of diisopropylethylamine in 10 ml of dichloromethane are added drop by drop. The mixture is allowed to rise to room temperature and is stirred for one night. The medium is then poured into water and extracted with dichloromethane. The organic phases are collected and washed with water. They are dried over sodium sulfate. The solvents are evaporated. The residue is chromatographed on silica gel (heptane/ethyl acetate 80/20) and 485 mg of N-(2,6-diisopropylphenyl)-2-(2-oxo-1-phenyl-1,3-diazaspiro[4.5]dec-3-yl)acetamide are obtained in the form of a white solid after having been precipitated in dichloromethane and heptane, filtered and dried. M.p. 107-9° C., yield=79%.

Aufarbeitung

  1. customto rise to room temperature
  2. extractionextracted with dichloromethane
  3. customThe organic phases are collected
  4. washwashed with water
  5. dry with materialThey are dried over sodium sulfate
  6. customThe solvents are evaporated
  7. customThe residue is chromatographed on silica gel (heptane/ethyl acetate 80/20) and 485 mg of N-(2,6-diisopropylphenyl)-2-(2-oxo-1-phenyl-1,3-diazaspiro[4.5]dec-3-yl)acetamide
  8. customare obtained in the form of a white solid
  9. customafter having been precipitated in dichloromethane
  10. filtrationheptane, filtered
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d8922995b38641ab9b79d516a1c97158
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08513307B2

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