N-(2-Hydroxyethyl)ethylenediamine → HCID 67181893, compound

HRID 1724827Notes

Reaction equation

HRID 1724827 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=O.[NH2:8][CH2:9][CH2:10][NH:11][CH2:12][CH2:13][OH:14]>C(O)C>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH:8][CH2:9][CH2:10][NH:11][CH2:12][CH2:13][OH:14]

Participants

4

Reactant 2

HCID 8112N-(2-Hydroxyethyl)ethylenediamineHCID 27349031,3-Thiazole-2-carbaldehyde

Product 1

HCID 67181893HCID 67181893, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3 Å molecular sieves (22.5 g) and a solution of 2-thiazole-carboxaldehyde (14.5 g, 128 mmol) in ethanol (90 ml) were sequentially added to a solution of 2-(2-aminoethylamino)ethanol (13.35 g, 128 mmol) in anhydrous ethanol. The reaction mixture was stirred for 4 hours, filtered through a pad of Celite while washing with ethanol (100 ml) and placed in a high-pressure flask. After adding acetic acid (3 ml) and Pd (10% on C, 2 g), the solution was introduced into Parr apparatus and, after several hydrogenation cycles, was stirred for 2 days under a hydrogen atmosphere at 40 psi. The reaction mixture was filtered through a pad of Celite, evaporated under vacuum and purified by flash chromatography (silica, 80/20/10 CH2Cl2/MeOH/NH3 eluent) to, give 2-[2-[(2-thiazolylmethyl)amino]ethylamino]ethanol (15.4 g, 60% yield) as a brown oil.

Workup

  1. filtrationfiltered through a pad of Celite
  2. washwhile washing with ethanol (100 ml)
  3. customplaced in a high-pressure flask
  4. additionAfter adding acetic acid (3 ml) and Pd (10% on C, 2 g)
  5. additionthe solution was introduced into Parr apparatus
  6. stirringafter several hydrogenation cycles, was stirred for 2 days under a hydrogen atmosphere at 40 psi
  7. filtrationThe reaction mixture was filtered through a pad of Celite
  8. customevaporated under vacuum
  9. custompurified by flash chromatography (silica, 80/20/10 CH2Cl2/MeOH/NH3 eluent) to,

Sources & evidence

ORD record
ord-287bf3add8f04707b80797648ab5cd67
Source dataset
uspto-grants-2009_02
Patent number
US07488811B2

Reaction notes

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