Sodium Iodide → 1-[N-(1-Azabicyclo[3.3.0]octan-5-yl)methyl-N-ethylamino]-4-nitronaphthalene

HRID 260920

Reaction equation

HRID 260920 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1.[CH2:15]([NH:17][CH2:18][C:19]12[CH2:26][CH2:25][CH2:24][N:23]1[CH2:22][CH2:21][CH2:20]2)[CH3:16].[I-].[Na+].[OH-].[Na+]>N1C=CC=CC=1>[N:23]12[CH2:24][CH2:25][CH2:26][C:19]1([CH2:18][N:17]([C:2]1[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1)[CH2:15][CH3:16])[CH2:20][CH2:21][CH2:22]2

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 3127191-Chloro-4-nitronaphthaleneHCID 10749640HCID 10749640, compound

Product 1

HCID 106170711-[N-(1-Azabicyclo[3.3.0]octan-5-yl)methyl-N-ethylamino]-4-nitronaphthaleneYield 30.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Chloro-4-nitronaphthalene (2.00 g, 9.63 mmol), 5-ethylaminomethyl-1-azabicyclo[3.3.0]octane (3.24 g, 19.3 mmol) and sodium iodide (580 mg) were added into anhydrous pyridine (20.0 ml) to react the mixture in a sealed tube for 20 hours at 190° C. After addition of aqueous sodium hydroxide solution subsequent to concentration in vacuo, the reaction mixture was extracted by ethyl acetate, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by column chromatography to afford the desired compound (1.00 g, 30.6%), as a yellow liquid.

Workup

  1. customto react the mixture in a sealed tube for 20 hours at 190° C
  2. concentrationsubsequent to concentration in vacuo
  3. extractionthe reaction mixture was extracted by ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-6e6833ec92c34b308874877b0333b085
Source dataset
uspto-grants-1996_06
Patent number
US05530138

Linked notes

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