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

HRID 416460Notes

Reaction equation

HRID 416460 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-2555f9b38d894c398a0263bd4482ec55
Source dataset
uspto-grants-2012_01
Patent number
US08088917B2

Reaction notes

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