Potassium Carbonate → 2-(Cyclopentylmethyl-ethyl-amino)-5,6,7,8-tetrahydro-quinoline-3-carbonitrile

HRID 577793Notes

Reaction equation

HRID 577793 reaction equation
Cl[C:2]1[C:11]([C:12]#[N:13])=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C@@H:20]1(N)[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]1[NH2:26].[CH:28]1(NCC)CCC[CH2:29]1>O1CCOCC1.[Cu]I>[CH:22]1([CH2:21][N:26]([CH2:28][CH3:29])[C:2]2[C:11]([C:12]#[N:13])=[CH:10][C:9]3[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=3[N:3]=2)[CH2:23][CH2:24][CH2:25][CH2:20]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 558581N-EthylcyclopentanamineHCID 37798182-Chloro-5,6,7,8-tetrahydroquinoline-3-carbonitrile

Product 1

HCID 574868292-(Cyclopentylmethyl-ethyl-amino)-5,6,7,8-tetrahydro-quinoline-3-carbonitrileYield 135.8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent2×

Procedure

Dry dioxane (15 mL) was added to a mixture of 2-chloro-5,6,7,8-tetrahydro-quinoline-3-carbonitrile (3.0 g, 15.62 mmol), potassium carbonate (8.6 g, 62.5 mmol), CuI (5 mol %, 0.064 g), and trans-1,2-cyclohexanediamine (5 mol %, 0.089 g) under an argon atmosphere. A solution of N-cyclopentyl-ethylamine (2.3 g, 18.75 mmol) in dioxane was them added to the stirred reaction mixture, which was then refluxed for 24 h. After this time, the solvent was evaporated under vacuum, and the residue was purified by column chromatography over silica gel (100-200 mesh), eluted with 2% ethyl acetate and petroleum ether, to afford 2-(cyclopentylmethyl-ethyl-amino)-5,6,7,8-tetrahydro-quinoline-3-carbonitrile (0.3 g), yield: 10%.

Workup

  1. additionadded to the stirred reaction mixture, which
  2. temperaturewas then refluxed for 24 h
  3. customAfter this time, the solvent was evaporated under vacuum
  4. customthe residue was purified by column chromatography over silica gel (100-200 mesh)
  5. washeluted with 2% ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-9db5cea5f67b4f37828ca260e40adb5e
Source dataset
uspto-grants-2015_05
Patent number
US09040558B2

Reaction notes

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