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

HRID 1702028Notes

Reaction equation

HRID 1702028 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:10]2([CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[CH2:9]1.C(=O)([O-])[O-].[K+].[K+].[N:29]#CBr>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:10]2([CH2:15][CH2:14][N:13]([C:16]#[N:29])[CH2:12][CH2:11]2)[CH2:9]1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 12801599HCID 12801599, compound

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-0b55201eda1c463e901782d888336fd1
Source dataset
uspto-grants-1983_04
Patent number
US04379932

Reaction notes

Loading…