1-Chloro-2-fluorobenzene → 6-Chloro-1-(2-chlorophenyl)-1'-methylspiro[indoline-3,4'-piperidine] maleate

HRID 1707118Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1707118
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][CH2:9][C:10]3([CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.[H-].[Na+].[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1F.[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31]>CS(C)=O.CCOCC>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31].[Cl:1][C:2]1[CH:7]=[C:6]2[N:8]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[Cl:19])[CH2:9][C:10]3([CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 95831-Chloro-2-fluorobenzeneHCID 24758Sodium hydrideHCID 444266Maleic AcidHCID 128016176-Chloro-1'-methylspiro[indoline-3,4'-piperidine]

Produkt 1

HCID 128016266-Chloro-1-(2-chlorophenyl)-1'-methylspiro[indoline-3,4'-piperidine] maleate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A mixture of 2.4 g of 6-chloro-1'-methylspiro[indoline-3,4'-piperidine], Example 23 b, 0.5 g of sodium hydride (99%) and 6 g of 2-chlorofluorobenzene in 25 ml of dimethylsulfoxide is stirred at 45° C. under nitrogen for 1 hour. Thereafter, the mixture is quenched with ice-water before being extracted thrice with ether. The combined ether extracts are successively washed with water, dried and concentrated under vacuum leaving a reddish oil. The oil is passed through an alumina column, ether eluant, and the purified oil, in ether, is converted to its maleic acid salt. The salt is recrystallized from an acetone-ether mixture to provide off-white platelets, mp 172°-173° C. of 6-chloro-1-(2-chlorophenyl)-1'-methylspiro[indoline-3,4'-piperidine] maleate.

Aufarbeitung

  1. customThereafter, the mixture is quenched with ice-water
  2. extractionbefore being extracted thrice with ether
  3. washThe combined ether extracts are successively washed with water
  4. customdried
  5. concentrationconcentrated under vacuum
  6. customleaving a reddish oil
  7. customThe salt is recrystallized from an acetone-ether mixture

Quellen und Nachweise

ORD-Eintrag
ord-8d642f26b50b4a50bf5ea6d43e18b568
Quelldatensatz
uspto-grants-1980_06
Patentnummer
US04209625

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