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Glutaric anhydride → 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-delta-oxo-1-piperidinepentanoic acid

HRID 845435
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 845435
C(N(C(C)C)C(C)C)C.[C:10]1(=[O:17])[O:16][C:14](=[O:15])[CH2:13][CH2:12][CH2:11]1.[CH:18]1[C:28]2[CH:27]=[CH:26][C:25]3[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=3[CH:23]([CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)[C:22]=2[CH:21]=[CH:20][CH:19]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:29]1[C:25]2[CH:26]=[CH:27][C:28]3[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=3[CH:23]([CH:33]3[CH2:34][CH2:35][N:36]([C:14](=[O:15])[CH2:13][CH2:12][CH2:11][C:10]([OH:16])=[O:17])[CH2:37][CH2:38]3)[C:24]=2[CH:32]=[CH:31][CH:30]=1
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Komponenten

6

Edukt 3

HCID 7940Glutaric anhydrideHCID 81531DiisopropylethylamineHCID 137534104-(5H-Dibenzo[a,d][7]annulen-5-yl)piperidine

Produkt 1

HCID 142533284-(5H-dibenzo[a,d]cyclohepten-5-yl)-delta-oxo-1-piperidinepentanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

0.04 gram (0.36 millimole) of 4-dimethylaminopyridine, 0.94 gram (7.26 millimoles) of ethyl diisopropylamine, and 0.41 gram (3.63 millimoles) of glutaric anhydride were added successively to a solution of 1.00 gram (3.63 millimoles) of 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-piperidine and the resulting mixture stirred at ambient temperature for two hours. The reaction mixture was diluted with 100 milliliters of methylene chloride and washed with aqueous hydrochloric acid and then with brine. The washed solution was dried over magnesium sulfate, the drying agent filtered and the solution evaporated in vacuo whereupon a foam was produced which when triturated with hot acetonitrile produced white crystals. The crystals were recrystallized from hot acetic acid/acetonitrile to obtain 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-δ-oxo-1-piperidinepentanoic acid product, m.p. 180°-186° C. The product had elemental analyses as follows:

Aufarbeitung

  1. washwashed with aqueous hydrochloric acid
  2. dry with materialThe washed solution was dried over magnesium sulfate
  3. filtrationthe drying agent filtered
  4. customthe solution evaporated in vacuo whereupon a foam
  5. customwas produced which when
  6. customtriturated with hot acetonitrile produced white crystals
  7. customThe crystals were recrystallized from hot acetic acid/acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-c42dab549b5941d09eae260fb4e34fd7
Quelldatensatz
uspto-grants-1988_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04758577

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