2-Chloroaniline → N-[2-(1-Azabicyclo[3.3.0]octan-5-yl)ethyl]-2-chloroaniline

HRID 260930Notes

Reaction equation

HRID 260930 reaction equation
[N+](C1C=CC=CC=1)([O-])=O.[Cl:10][C:11]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1[NH2:13].Cl[CH2:19][CH2:20][C:21]12[CH2:28][CH2:27][CH2:26][N:25]1[CH2:24][CH2:23][CH2:22]2.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>>[N:25]12[CH2:26][CH2:27][CH2:28][C:21]1([CH2:20][CH2:19][NH:13][C:12]1[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=1[Cl:10])[CH2:22][CH2:23][CH2:24]2

Participants

6

Reactant 5

HCID 72402-ChloroanilineHCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 107023655-(2-Chloroethyl)-1-azabicyclo[3.3.0]octane

Product 1

HCID 10587741N-[2-(1-Azabicyclo[3.3.0]octan-5-yl)ethyl]-2-chloroanilineYield 40.1%

Procedure

To nitrobenzene (30.0 ml), 2-chloroaniline (600 mg, 4.70 mmol), 5-(2-chloroethyl)-1-azabicyclo[3.3.0]octane (hydrochloride, 1.98 g, 9.42 mmol) and anhydrous potassium carbonate (3.90 g, 28.2 mmol) were added to react same for 10 hours at 120° C. subsequent to addition of 10% aqueous sodium hydroxide solution, the reaction mixture was extracted by ethyl acetate, washed by sodium chloride solution, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by column chromatography to afford the desired compound (499 mg, 40.1%), as a colorless liquid.

Workup

  1. extractionthe reaction mixture was extracted by ethyl acetate
  2. washwashed by sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-0c1f829bce154434a3551583abc00153
Source dataset
uspto-grants-1996_06
Patent number
US05530138

Reaction notes

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