Hydrochloric Acid → 5,5-Dimethyl-10-[4-(morpholino)butyryloxy]-8-(3-methyl-2-octyl)-2-(2-propynyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d] pyridine dihydrochloride

HRID 441880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 441880
[CH3:1][C:2]1([CH3:29])[C:21]2[CH2:22][CH2:23][N:24]([CH2:26][C:27]#[CH:28])[CH2:25][C:20]=2[C:5]2[C:6]([OH:19])=[CH:7][C:8]([CH:10]([CH:12]([CH3:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:11])=[CH:9][C:4]=2[O:3]1.[ClH:30].[O:31]1[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][CH2:39][C:40](O)=[O:41])[CH2:33][CH2:32]1.C1(N=C=NC2CCCCC2)CCCCC1.C(NC1CCCCC1)(NC1CCCCC1)=O.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.Cl>CO.C(Cl)(Cl)Cl.CCOCC.C(Cl)Cl>[ClH:30].[ClH:30].[CH3:29][C:2]1([CH3:1])[C:21]2[CH2:22][CH2:23][N:24]([CH2:26][C:27]#[CH:28])[CH2:25][C:20]=2[C:5]2[C:6]([O:19][C:40](=[O:41])[CH2:39][CH2:38][CH2:37][N:34]3[CH2:33][CH2:32][O:31][CH2:36][CH2:35]3)=[CH:7][C:8]([CH:10]([CH:12]([CH3:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:11])=[CH:9][C:4]=2[O:3]1

Komponenten

10

Edukt 6

HCID 313Hydrochloric AcidHCID 4277N,N'-DicyclohexylureaHCID 10868DicyclohexylcarbodiimideHCID 990408-(1,2-Dimethylheptyl)-1,3,4,5-tetrahydro-5,5-dimethyl-2-(2-propyn-1-yl)-2H-(1)benzopyrano(4,3-c)pyridin-10-olHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 127337464-Morpholin-4-Yl-Butyric Acid Hydrochloride

Produkt 1

HCID 214339055,5-Dimethyl-10-[4-(morpholino)butyryloxy]-8-(3-methyl-2-octyl)-2-(2-propynyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d] pyridine dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 21584188Chloroform methanolLösungsmittel

Versuchsvorschrift

4.0 g. (10.1 mm.) of 5,5-dimethyl-10-hydroxy-8-(3-methyl-2-octyl)-2-(2-propynyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d]pyridine, 2.10 g. (10.1 mm.) of γ-morpholinobutyric acid hydrochloride and 2.18 g. (10.6 mm.) of dicyclohexylcarbodiimide were added to 200 ml. of methylene chloride. The reaction mixture was stirred at room temperature for 16 hours and after cooling the by-product of dicyclohexylurea was removed by suction filtration. The mother liquor was evaporated to give a residue which after the usual work-up was converted to a dihydrochloride by the addition of an ether solution of hydrogen chloride. Recrystallization from methylene chloride/diethyl ether gave a total of 3.23 g. (52%), m.p. 154°-160° C. The nuclear magnetic resonance and infrared spectra were in agreement with the proposed structure; the material was pure by thin layer chromatography (10% MeOH/CHCl3).

Aufarbeitung

  1. customwas removed by suction filtration
  2. customThe mother liquor was evaporated
  3. customto give a residue which after the usual work-up
  4. customRecrystallization from methylene chloride/diethyl ether
  5. customgave a total of 3.23 g

Quellen und Nachweise

ORD-Eintrag
ord-ffec0653f03e40a9aa289242c9eec6fd
Quelldatensatz
uspto-grants-1977_08
Patentnummer
US04042694

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