Benzaldehyde → N-Benzyl-N'-boc-ethylenediamine

HRID 85367Notes

Reaction equation

HRID 85367 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[O-]S([O-])(=O)=O.[Mg+2].CCN(CC)CC>>[CH2:12]([NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 187201N-BOC-ethylenediamine

Product 1

HCID 10634443N-Benzyl-N'-boc-ethylenediamineYield 25.1%

Procedure

To a solution of tert-butyl 2-aminoethylcarbamate (3.7 g, 22.3 mmol), benzaldehyde (2.36 g, 22.3 mmol) and MgSO4 (1.33 g) in 1,2-dicholoroethane (300 mL) and Et3N (3.1 mL, 22.3 mmol) at RT was added NaHB(AcO)3. The mixture was stirred (RT, 16 h) and filtered. The solution was washed with saturated aqueous NaHCO3 (200 mL), dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel, eluting with MeOH-DCM (0-10%) to afford tert-butyl 2-(benzylamino)ethylcarbamate (1.4 g, 23%). Mass calculated for C14H22N2O2=250.34; found: [M+H]+=251.3.

Workup

  1. filtrationfiltered
  2. washThe solution was washed with saturated aqueous NaHCO3 (200 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by chromatography on silica gel
  6. washeluting with MeOH-DCM (0-10%)

Sources & evidence

ORD record
ord-023be025fcb34bd6bd1adfa2fdd08f55
Source dataset
uspto-grants-2014_09
Patent number
US08846972B2

Reaction notes

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