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

HRID 647261Notes

Reaction equation

HRID 647261 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-f68cb9ba1ad54cc7805ef39da05b8c6d
Source dataset
uspto-grants-1983_10
Patent number
US04408050

Reaction notes

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