Oxalic Acid → HCID 21268306, Verbindung

HRID 1900997Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1900997
ClCCC[O:5]C1C2C=CNC=2C=CC=1.[CH:15]1([CH2:18][O:19][C:20]2[CH:28]=[CH:27][CH:26]=[C:25]3[C:21]=2[C:22]([CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:23][NH:24]3)[CH2:17][CH2:16]1.[CH:35]1([CH2:38][O:39][C:40]2[CH:48]=[CH:47][CH:46]=[C:45]3[C:41]=2[CH:42]=[CH:43][NH:44]3)C[CH2:36]1.Cl.O.N1CCC(=O)CC1.[OH-].[K+].[C:60]([OH:65])(=[O:64])[C:61]([OH:63])=[O:62]>[Pd].CO.C(OCC)(=O)C>[OH2:5].[C:60]([OH:65])(=[O:64])[C:61]([OH:63])=[O:62].[NH:44]1[C:45]2[C:41](=[C:40]([O:39][CH2:38][CH2:35][CH2:36][N:32]3[CH2:33][CH2:34][CH:29]([C:22]4[C:21]5[C:25](=[CH:26][CH:27]=[CH:28][C:20]=5[O:19][CH2:18][CH:15]5[CH2:16][CH2:17]5)[NH:24][CH:23]=4)[CH2:30][CH2:31]3)[CH:48]=[CH:47][CH:46]=2)[CH:42]=[CH:43]1

Komponenten

10

Edukt 6

HCID 971Oxalic AcidHCID 14797Potassium HydroxideHCID 2723901PiperonylamineHCID 116941694-(3-chloropropoxy)-1H-indoleHCID 19956046HCID 19956046, VerbindungHCID 212682944-Cyclopropylmethoxyindole

Produkt 1

HCID 21268306HCID 21268306, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

The title compound was prepared according to Example 99 from 1-chloro-3-(1H-indole-4-oxy)propane and 4-(4-cyclopropylmethoxy-1H-indol-3-yl)piperidine (which was prepared by condensing 4-cyclopropylmethoxyindole with 4-piperidone monohydrate hydrochloride in refluxing methanol with potassium hydroxide, followed by reduction of the unsaturation with palladium on carbon in methanol). The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 57% overall yield as a white foam . FDMS m/e=443 (M+ of free base).

Aufarbeitung

  1. customoverall yield as a white foam

Quellen und Nachweise

ORD-Eintrag
ord-524dd8339d1d4c3a876eba20a4e4ce9e
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576321

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