Sodium hydride → [2-(dibenzylamino)-5,6-dihydro-7H-cyclopenta[b]pyridin-7-ylidene]acetonitrile

HRID 887768Notes

Reaction equation

HRID 887768 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH2:14]([N:21]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:22]1[N:27]=[C:26]2[C:28](=O)[CH2:29][CH2:30][C:25]2=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1.[Cl-].[NH4+].C(OCC)(=O)C>[CH2:14]([N:21]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:22]1[N:27]=[C:26]2[C:28](=[CH:5][C:3]#[N:4])[CH2:29][CH2:30][C:25]2=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 591459342-(dibenzylamino)-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one

Product 1

HCID 68702395[2-(dibenzylamino)-5,6-dihydro-7H-cyclopenta[b]pyridin-7-ylidene]acetonitrileYield 95%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a suspension of 60% sodium hydride (146 mg, 3.65 mmol) in tetrahydrofuran (20 mL) was added diethyl cyanomethylphosphonate (640 μL, 3.96 mmol), and the mixture was stirred at room temperature for 15 min. A solution of 2-(dibenzylamino)-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one (1.00 g, 3.04 mmol) in tetrahydrofuran (10 mL) was added thereto, and the mixture was further stirred for 15 min. The reaction solution was diluted with saturated aqueous ammonium chloride solution, diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→30/70) to give the title compound (1.01 g, yield 95%).

Workup

  1. stirringthe mixture was further stirred for 15 min
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→30/70)

Sources & evidence

ORD record
ord-da540c9c8fd24de8aacbac0954eceef3
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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