4-Bromopyridine → 1-pyridin-4-yl-1,4-diazepane

HRID 1243329Notes

Reaction equation

HRID 1243329 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[NH:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[OH-].[Na+]>O>[N:5]1[CH:6]=[CH:7][C:2]([N:8]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 142684-BromopyridineHCID 14798Sodium HydroxideHCID 68163Hexahydro-1,4-diazepine

Product 1

HCID 27605081-pyridin-4-yl-1,4-diazepaneYield 40.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2 g of 4-bromopyridine and 10 g of homopiperazine is heated at 100° C. for 4 hours. 100 ml of water are added to the reaction mixture and the resulting mixture is basified to pH 10 by addition of 10% NaOH solution and extracted three times with 100 ml of chloroform, the organic phase is dried over Na2SO4 and the solvent is evaporated off under vacuum. 0.9 g of the expected product is obtained.

Workup

  1. extractionextracted three times with 100 ml of chloroform
  2. dry with materialthe organic phase is dried over Na2SO4
  3. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-e45bd25b6bab40cb95ed25343601ba20
Source dataset
uspto-grants-2006_10
Patent number
US07119086B2

Reaction notes

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