Triethylamine → 3-((2-Nitrobenzyl)amino)propan-1-ol

HRID 553401Notes

Reaction equation

HRID 553401 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[N+:13]([C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18]Cl)([O-:15])=[O:14].O.Cl>O1CCCC1>[N+:13]([C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][NH:1][CH2:2][CH2:3][CH2:4][OH:5])([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 90863-Amino-1-propanolHCID 119212-Nitrobenzyl chlorideHCID 21885828Hydrate;hydrochloride

Product 1

HCID 287156543-((2-Nitrobenzyl)amino)propan-1-olYield 33.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Aminopropanol (3.94 g, 52.5 mmol) and triethylamine (1.77 g, 17.5 mmol) were dissolved in tetrahydrofuran (30 ml) and added with 2-nitrobenzyl chloride (3.00 g, 17.5 mmol) at room temperature. After heated to reflux for seven hours, the reaction mixture was allowed to cool and poured into 1N hydrochloric acid water and extracted with ether. The aqueous layer was adjusted to pH 9 with a saturated sodium hydrogen carbonate aqueous solution and then extracted with ethyl acetate. The organic layer was washed with a saturated brine and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 3-(2-nitrobenzylamino)propanol (1.22 g).

Workup

  1. temperatureAfter heated
  2. temperatureto reflux for seven hours
  3. temperatureto cool
  4. extractionextracted with ether
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with a saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9355c83804f84ceca67ec9a7ac6706c6
Source dataset
uspto-grants-2011_11
Patent number
US08048825B2

Reaction notes

Loading…