Cyanogen Bromide → 1-(4-Chlorophenyl)-1'-cyanospiro[indoline-3,4'-piperidine]

HRID 1702091Notes

Reaction equation

HRID 1702091 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:10]3([CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]3)[CH2:9]2)=[CH:4][CH:3]=1.[N:23]#CBr.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:10]3([CH2:15][CH2:14][N:13]([C:16]#[N:23])[CH2:12][CH2:11]3)[CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 128015891-(4-Chlorophenyl)-1'-methylspiro[indoline-3,4'-piperidine]

Product 1

HCID 128016111-(4-Chlorophenyl)-1'-cyanospiro[indoline-3,4'-piperidine]

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.95 g of 1-(4-chlorophenyl)-1'-methylspiro[indoline-3,4'-piperidine] (Example 2), 0.42 g of cyanogen bromide and 1 g of potassium carbonate in 25 ml of dichloromethane is stirred at ambient temperature for two hours. The reaction mixture is filtered and the filtrate concentrated to dryness leaving an oily residue which is crystallized from an acetone-hexane mixture leaving colorless crystals, mp 178.5°-180° C. of 1-(4-chlorophenyl)-1'-cyanospiro[indoline-3,4'-piperidine].

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate concentrated to dryness
  3. customleaving an oily residue which
  4. customis crystallized from an acetone-hexane mixture

Sources & evidence

ORD record
ord-35a1ed98e49a4c309aad18b8774e6749
Source dataset
uspto-grants-1983_04
Patent number
US04379933

Reaction notes

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