Hexamethylenediamine → N-(6-Aminohexyl)-4-azidobenzamide

HRID 617682Notes

Reaction equation

HRID 617682 reaction equation
C1C(=O)N(O[C:9]([C:11]2[CH:16]=[CH:15][C:14]([N:17]=[N+:18]=[N-:19])=[CH:13][CH:12]=2)=[O:10])C(=O)C1.[NH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH2:27]>C1COCC1>[N:17]([C:14]1[CH:13]=[CH:12][C:11]([C:9]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH2:27])=[O:10])=[CH:16][CH:15]=1)=[N+:18]=[N-:19]

Participants

4

Reactant 2

HCID 16402HexamethylenediamineHCID 122153Hydroxysuccinimidyl-4-azidobenzoate

Product 1

HCID 13330101N-(6-Aminohexyl)-4-azidobenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.6 g (10 mmol) HSAB 1 are dissolved in 70 ml THF and dropwise added to solution of 11.62 g (100 mmol) of hexamethylene diamine in THF under stirring and cooled on ice. Subsequently, the ice bath is removed and the temperature is allowed to adjust to room temperature. The solvent is drawn off on the rotation evaporator and excess hexymethylene diamine is removed in a high vacuum as far as possible. The remaining raw product is digested for 20 min in 100 ml of water and subsequently dried overnight in an exsiccator. Product 2b is a slightly yellow to brown solid material.

Workup

  1. temperaturecooled on ice
  2. customSubsequently, the ice bath is removed
  3. customto adjust to room temperature
  4. customThe solvent is drawn off on the rotation evaporator and excess hexymethylene diamine
  5. customis removed in a high vacuum as far as possible

Sources & evidence

ORD record
ord-4f0aff6839d54275a7d6139633bbd97f
Source dataset
uspto-grants-1999_09
Patent number
US05952185

Reaction notes

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