Methanol → 1-(1-Methyl-3-indolyl)cyclopentaneacetonitrile

HRID 1587716Notes

Reaction equation

HRID 1587716 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2([CH:16]=O)[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:3]1.C(C1C=C(C(C)C)C=C(C(C)C)C=1S(NN)(=O)=O)(C)C.[C-:38]#[N:39].[K+].CO>O1CCCC1.O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2([CH2:16][C:38]#[N:39])[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:3]1

Participants

7

Reactant 4

HCID 887MethanolHCID 9032Potassium CyanideHCID 3593332,4,6-TriisopropylbenzenesulphonohydrazideHCID 105612721-(1-Methyl-3-indolyl)cyclopentanecarbaldehyde

Product 1

HCID 107524351-(1-Methyl-3-indolyl)cyclopentaneacetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.9 g (0.0134 mol) of 1-(1-methyl-3-indolyl)-cyclopentanecarbaldehyde and 5 g (0.0166 mol) of 2,4,6-triisopropylbenzenesulphonohydrazide dissolved in 30 cm3 of tetrahydrofuran are stirred at room temperature for 3 hours. The tetrahydrofuran is thereafter evaporated off completely and 2.6 g (0.0402 mol) of potassium cyanide and 30 cm3 of methanol are added to the residue. The mixture is heated to reflux for 4.5 hours and then cooled, water is added and the mixture is extracted with dichloromethane. In succession, the organic extract obtained is washed with aqueous sodium hydrogen carbonate solution, dried over sodium sulphate and filtered and the solvent is evaporated off. The crude product thereby isolated is purified by chromatography on a silica gel column in dichloromethane and then, where appropriate, by flash chromatography using a 3:1 hexane/ethyl acetate mixture as eluent.

Workup

  1. customThe tetrahydrofuran is thereafter evaporated off completely
  2. temperatureThe mixture is heated
  3. temperatureto reflux for 4.5 hours
  4. temperaturecooled
  5. extractionthe mixture is extracted with dichloromethane
  6. extractionIn succession, the organic extract
  7. customobtained
  8. washis washed with aqueous sodium hydrogen carbonate solution
  9. dry with materialdried over sodium sulphate
  10. filtrationfiltered
  11. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-c69ebea46139456e88f2e5a007385928
Source dataset
uspto-grants-1993_06
Patent number
US05219859

Reaction notes

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