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

HRID 1660359노트

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HRID 1660359 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-3161036af53d45eeac9ab2c92c5f7535
출처 데이터셋
uspto-grants-1981_12
특허 번호
US04307235

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