Pyridine → 2-[2-(1-Azabicyclo[3.3.0]octan-5-yl)ethylamino]benzonitrile

HRID 260928Notes

Reaction equation

HRID 260928 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[N:10]12[CH2:17][CH2:16][CH2:15][C:14]1([CH2:18][CH2:19][NH2:20])[CH2:13][CH2:12][CH2:11]2.N1C=CC=CC=1>O>[N:10]12[CH2:17][CH2:16][CH2:15][C:14]1([CH2:18][CH2:19][NH:20][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[CH2:13][CH2:12][CH2:11]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 678552-FluorobenzonitrileHCID 107969772-(Hexahydro-1H-pyrrolizin-7a-yl)ethanamine

Product 1

HCID 107535222-[2-(1-Azabicyclo[3.3.0]octan-5-yl)ethylamino]benzonitrileYield 95.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Fluorobenzonitrile (1.00 g, 8.26 mmol) and 2-(1-azabicyclo[3.3.0]octan-5-yl)ethylamine (3.15 g, 20.4 mmol) were added into anhydrous pyridine (10.0 ml) to react the mixture in a sealed tube for 10.5 hours at 180° C. After addition of water subsequent to concentration in vacuo, the reaction mixture was extracted by ethyl acetate, dried over anhydrous sodium sulfate, concentrated in vacuo, and refined by column chromatography to afford the desired compound (2.02 g, 95.8%), as a colorless liquid.

Workup

  1. customto react the mixture in a sealed tube for 10.5 hours at 180° C
  2. concentrationto concentration in vacuo
  3. extractionthe reaction mixture was extracted by ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc2793cb99ee48efbbc4e595b548bf94
Source dataset
uspto-grants-1996_06
Patent number
US05530138

Reaction notes

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