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

HRID 647251Notes

Reaction equation

HRID 647251 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-93bba3076b854442a8f2e8cf99498fb8
Source dataset
uspto-grants-1983_10
Patent number
US04408050

Reaction notes

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