Triethylamine → 2-(3-Azabicyclo[3.1.0]hex-3-yl)-5-nitropyridine

HRID 1690074Notes

Reaction equation

HRID 1690074 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH:11]12[CH2:17]C[CH:15]1[CH2:14][NH:13][CH2:12]2.C(N(CC)CC)C>O1CCOCC1>[CH:15]12[CH2:17][CH:11]1[CH2:12][N:13]([C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)[CH2:14]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783082-Chloro-5-nitropyridineHCID 219625873-Azabicyclo[3.2.0]heptane

Product 1

HCID 574315302-(3-Azabicyclo[3.1.0]hex-3-yl)-5-nitropyridineYield 97.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 0.5 g (3.15 mmol) of 2-chloro-5-nitropyridine, 0.452 g (3.78 mmol) of 3-aza-bicyclo[3.2.0]heptane (J. Med. Chem. 1967, 10(4), 621) and 1.32 mL (6.94 mmol) of triethylamine in 10 mL of dioxane, is heated at 65° C. for 4 h. The reaction mixture is then poured into 50 mL of ice water. The mixture is stirred until the ice has melted completely, then a yellow precipitate is collected by filtration and is dried at reduced pressure. In this way we isolate 0.63 g of the expected product in the form of a yellow powder.

Workup

  1. filtrationa yellow precipitate is collected by filtration
  2. customis dried at reduced pressure

Sources & evidence

ORD record
ord-325ad600fd39436488c3f5d149b51b6c
Source dataset
uspto-grants-2012_04
Patent number
US08153650B2

Reaction notes

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