Acetic Acid → HCID 58859150, compound

HRID 1349459Notes

Reaction equation

HRID 1349459 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+].[Cl:35][C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][C:43]=1[Cl:44])[CH:39]=O>C(Cl)(Cl)Cl>[Cl:35][C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][C:43]=1[Cl:44])[CH2:39][NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 227103,4-DichlorobenzaldehydeHCID 187201N-BOC-ethylenediamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 58859150HCID 58859150, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

tert-Butyl N-(2-aminoethyl)carbamate (1.51 g) was dissolved in chloroform (20 ml) and 3,4-dichlorobenzaldehyde (1.65 g), acetic acid (0.54 ml) and sodium triacetoxyborohydride (2.6 g) were added at room temperature. The mixture was stirred overnight. Saturated aqueous sodium hydrogen carbonate solution was added to the obtained reaction mixture and the mixture was stirred and extracted three times with chloroform. The combined organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=9:1) to give tert-butyl [2-(3,4-dichlorobenzylamino)ethyl]carbamate (2.1 g).

Workup

  1. stirringthe mixture was stirred
  2. extractionextracted three times with chloroform
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated
  6. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-275ea5a9cb754e7db7b1cd14ea368623
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

Loading…