Cyanogen Bromide → 1-(2-Chlorophenyl)-1'-cyanospiro(indoline3,4'-piperidine)

HRID 647267Notes

Reaction equation

HRID 647267 reaction equation
C(O)(=O)/C=C\C(O)=O.[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]2([CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)[CH2:17]1.C(=O)([O-])[O-].[K+].[K+].[N:37]#CBr>C(Cl)(Cl)Cl>[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]2([CH2:23][CH2:22][N:21]([C:24]#[N:37])[CH2:20][CH2:19]2)[CH2:17]1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 128016001-(2-Chlorophenyl)-1'-methylspiro[indoline-3,4'-piperidine] maleate

Product 1

HCID 128016161-(2-Chlorophenyl)-1'-cyanospiro(indoline3,4'-piperidine)

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 1.0 g of 1-(2-chlorophenyl)-1'-methylspiro[indoline-3,4'-piperidine] of Example 17 in 16 ml of dry chloroform is added 2.4 g of anhydrous potassium carbonate and 0.73 g of cyanogen bromide. The reaction is stirred 7 hours at room temperature and then is filtered through paper. Approximately one ml of methanol is added and the solution is rotary evaporated to a glass. The glass is chromatographed on 80 cc of silica gel with 1:1, ether:dichloromethane to give a crystalline solid. The solid is recrystallized thrice from acetone-hexane to give a solid of 1-(2-chlorophenyl)-1'-cyanospiro(indoline-3,4'-piperidine), mp 157.5°-159.5° C.

Workup

  1. filtrationis filtered through paper
  2. additionApproximately one ml of methanol is added
  3. customthe solution is rotary evaporated to a glass
  4. customThe glass is chromatographed on 80 cc of silica gel with 1:1, ether
  5. customdichloromethane to give a crystalline solid
  6. customThe solid is recrystallized thrice from acetone-hexane

Sources & evidence

ORD record
ord-c1ae79b00c2c4b3fa051ba624300e237
Source dataset
uspto-grants-1983_10
Patent number
US04408050

Reaction notes

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