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

HRID 1632859Notes

Reaction equation

HRID 1632859 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

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].

Workup

  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

Sources & evidence

ORD record
ord-f816751c53bd4d7d87ae429d44c6fa46
Source dataset
uspto-grants-1984_10
Patent number
US04477667

Reaction notes

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