Cyanogen Bromide → 6-Chloro-1'-cyano-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine]

HRID 67219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 67219
[Cl:1][C:2]1[CH:7]=[C:6]2[N:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-:25])=[O:24])[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.[N:26]#CBr.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]2[N:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-:25])=[O:24])[CH2:9][C:10]3([CH2:15][CH2:14][N:13]([C:16]#[N:26])[CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 128016276-Chloro-1'-methyl-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine]

Produkt 1

HCID 128016286-Chloro-1'-cyano-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine]

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 3.2 g of 6-chloro-1'-methyl-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine], Example 30, 2.0 g of cyanogen bromide and 6.0 g of potassium carbonate in 100 ml of chloroform is stirred at ambient temperature for 6 hours. Thereafter, the mixture is sequentially quenched with water, extracted with dilute sodium hydroxide and dried. The chloroform is removed under reduced pressure and the residue is passed through a silica gel column, ether eluant, providing an orange oil which crystallizes upon standing. The solid is recrystallized from an acetone-hexane mixture to provide orange prisms, mp 163°-165° C. of 6-chloro-1'-cyano-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine].

Aufarbeitung

  1. customThereafter, the mixture is sequentially quenched with water
  2. extractionextracted with dilute sodium hydroxide
  3. customdried
  4. customThe chloroform is removed under reduced pressure
  5. customproviding an orange oil which
  6. customcrystallizes
  7. customThe solid is recrystallized from an acetone-hexane mixture

Quellen und Nachweise

ORD-Eintrag
ord-7f9b12e94117487383fcfc1cbcc1fd0f
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04345081

Notizen zur Reaktion

Wird geladen…