1,5-Dibromopentane → 6-Azaspiro[5.6]dodecan-6-ium bromide

HRID 2360538Notes

Reaction equation

HRID 2360538 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]Br.[NH:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>O.[OH-].[Na+]>[Br-:1].[CH2:2]1[N+:8]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 81001,5-DibromopentaneHCID 8119Azepane

Product 1

HCID 173656566-Azaspiro[5.6]dodecan-6-ium bromide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

A slight excess of 1,5-dibromopentane was added dropwise to a solution of azepane and sodium hydroxide in water and stirred at reflux for several hours. The solution was then cooled to room temperature and diluted with aqueous sodium hydroxide. The reaction mixture was then extracted with chloroform, washed with water several times and evaporated to dryness to yield the white solid 6-azonia-spiro[5,6]dodecane bromide with a melting point of 260° C. 1H-NMR (300 MHz, D2O) δ 1.50 (m, 6H, CH2), 1.75 (m, 8H, CH2), 3.20 (t, 4H, N—CH2), 3.30 (t, 4H, N—CH2).

Workup

  1. temperatureat reflux for several hours
  2. extractionThe reaction mixture was then extracted with chloroform
  3. washwashed with water several times
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-6c23bac368444b56bef4a2979c8962db
Source dataset
uspto-grants-2014_04
Patent number
US08686134B2

Reaction notes

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