Sodium Hydroxide → HCID 15491645, compound

HRID 1859272Notes

Reaction equation

HRID 1859272 reaction equation
[C:1]([CH2:3][N:4]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]#[N:15])[CH2:9][CH2:8][N:7]([CH2:16][C:17]#[N:18])[CH2:6][CH2:5]1)#[N:2].B.C1COCC1.[OH-].[Na+]>C1COCC1.Cl.O>[NH2:15][CH2:14][CH2:13][N:10]1[CH2:11][CH2:12][N:4]([CH2:3][CH2:1][NH2:2])[CH2:5][CH2:6][N:7]([CH2:16][CH2:17][NH2:18])[CH2:8][CH2:9]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 15491644HCID 15491644, compound

Product 1

HCID 15491645HCID 15491645, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1,4,7-tris(cyanomethyl)-1,4,7-triazacyclononane (0.320 g, 1.23 mmol) and BH3.THF 1 M solution in THF (40 cm3) were refluxed under nitrogen for 48 h. After cooling, excess borane was destroyed by adding water (5 cm3), then the solution was dried under vacuum. The white solid obtained was dissolved in 50 cm3 of HCl 7M and heated under reflux for 40 h. After cooling, the solution was dried in vacuum to yield a white solid. The solid was dissolved in the minimum amount of water and the solution obtained was passed through a Dowex 1×8-200 column (10 g) activated with a solution 1M of sodium hydroxide. The solvent was removed under reduced pressure to yield a colourless oil. (0.270 g, 1.045 mmol) Yield: 85%.

Workup

  1. temperatureAfter cooling
  2. customexcess borane was destroyed
  3. additionby adding water (5 cm3)
  4. customthe solution was dried under vacuum
  5. customThe white solid obtained
  6. temperatureheated
  7. temperatureunder reflux for 40 h
  8. temperatureAfter cooling
  9. customthe solution was dried in vacuum
  10. customto yield a white solid
  11. customthe solution obtained
  12. customThe solvent was removed under reduced pressure
  13. customto yield a colourless oil

Sources & evidence

ORD record
ord-6e3618a97b9b4ac0a8cef7eee3397a47
Source dataset
uspto-grants-2000_11
Patent number
US06153775

Reaction notes

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