Tris(2-aminoethyl)amine → HCID 72359623, compound

HRID 480666

Reaction equation

HRID 480666 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH2:8][CH2:9][NH2:10])[CH2:5][CH2:6][NH2:7].C(=O)(O)[O-].[Na+].Cl[C:17]([CH3:23])([CH3:22])[CH:18]([N:20]=[O:21])[CH3:19]>C(#N)C>[CH3:22][C:17]([CH3:23])([NH:1][CH2:2][CH2:3][N:4]([CH2:8][CH2:9][NH2:10])[CH2:5][CH2:6][NH:7][C:17]([CH3:23])([CH3:22])[C:18](=[N:20][OH:21])[CH3:19])[C:18](=[N:20][OH:21])[CH3:19]

Participants

5

Reactant 3

HCID 77731Tris(2-aminoethyl)amineHCID 516892Sodium BicarbonateHCID 108663862-Chloro-2-methyl-3-nitrosobutane

Product 1

HCID 72359623HCID 72359623, compoundYield 9.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of tris-(2-aminoethyl)amine (1 ml, 6.68 mmol) in acetonitrile (10 ml) was added sodium bicarbonate (1.12 g, 13.36 mmol, 2 eq). A solution of 3-chloro-3-methyl-2-nitrosobutane (1.359 g, 10.02 mmol, 1.5 eq) in dry acetonitrile (5 ml) was added slowly. The reaction mixture was left to stir at room temperature for 3 days, and then filtered. The residue was washed well with acetonitrile, and the filtrate evaporated. The crude product was then purified by RP-HPLC (System L) to afford Compound 15 (164 mg, 7%).

Workup

  1. waitThe reaction mixture was left
  2. filtrationfiltered
  3. washThe residue was washed well with acetonitrile
  4. customthe filtrate evaporated
  5. customThe crude product was then purified by RP-HPLC (System L)

Sources & evidence

ORD record
ord-8344cf40307c48dfb48c0f21dd0d9540
Source dataset
uspto-grants-2003_11
Patent number
US06653299B1

Linked notes

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