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

HRID 1702103

Reaction equation

HRID 1702103 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]2([CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[CH2:11]1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[N:31]#CBr>C(Cl)(Cl)Cl>[C:18]([N:15]1[CH2:16][CH2:17][C:12]2([C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])[CH2:11]2)[CH2:13][CH2:14]1)#[N:31]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 128015961'-Methyl-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine]

Product 1

HCID 128016151'-Cyano-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine]

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 18.23 g of 1-(2-nitrophenyl)-1'-methylspiro[indoline-3,4'-piperidine] of Example 15 in 100 ml of chloroform is added dropwise over 50 minutes to a rapidly stirred slurry of 11.65 g of potassium carbonate and 8.94 g of cyanogen bromide in 100 ml of chloroform under nitrogen. After heating at reflux for 2.75 hours, the cooled product is washed with 10% sodium hydroxide and water, dried over anhydrous magnesium sulfate and concentrated to yield a crude solid which is chromatographed on silica gel (650 g) using ether-chloroform and is then recrystallized from ether-dichloromethane to yield a solid, mp 148°-150° C. of 1'-cyano-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine].

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 2.75 hours
  3. washthe cooled product is washed with 10% sodium hydroxide and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto yield a crude solid which
  7. customis chromatographed on silica gel (650 g)
  8. customis then recrystallized from ether-dichloromethane

Sources & evidence

ORD record
ord-6d38d2af100d41eb9cc2c22339070d16
Source dataset
uspto-grants-1983_04
Patent number
US04379933

Linked notes

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