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

HRID 1911763
Notes
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Reaction equation

HRID 1911763 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-84a4e8cb6d6448aaafcf908ad1d2c34f
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08604055B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes