N-(2-aminoethyl)acetamide → N-Acetyl-N'-[2-(phenylmethoxy)-2-oxoethyl]ethylenediamine

HRID 482936Notes

Reaction equation

HRID 482936 reaction equation
[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:4])[CH:2]=O.[C:13]([NH:16][CH2:17][CH2:18][NH2:19])(=[O:15])[CH3:14]>O1CCCC1>[C:13]([NH:16][CH2:17][CH2:18][NH:19][CH2:2][C:1]([O:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:4])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 11008258Benzyl glyoxylate

Product 1

HCID 20243518N-Acetyl-N'-[2-(phenylmethoxy)-2-oxoethyl]ethylenediamineYield 38.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Benzyl glyoxylate (3.28 g, 20.0 mmol) in dry tetrahydrofuran (15 ml) was added dropwise in monoacetylethylenediamine (1.53 g, 15 mmol) in dry tetrahydrofuran (60 ml) at room temperature. After 2 hours, the tetrahydrofuran was removed under vacuum, and the residue was dissolved in dry methanol (100 ml). Upon cooling to 0° C., 1.55 g of sodium cyanoborohydride was added, immediately followed by dropwise addition of 1.54 ml of acetic acid. The reaction was allowed to warm to room temperature and stirred for 40 minutes. The volatiles were removed under vacuum, and the residue was extracted from aqueous sodium bicarbonate with ethyl acetate. The combined organic layers were dried with sodium sulfate, and the volatiles were removed. The residue was purified by column chromatography on silica (LPS-1) (loading with 2% methanol/dichloromethane and eluting with 5% methanol/dichloromethane to yield 1.46 g of the title compound.

Workup

  1. customthe tetrahydrofuran was removed under vacuum
  2. dissolutionthe residue was dissolved in dry methanol (100 ml)
  3. addition1.55 g of sodium cyanoborohydride was added
  4. additionimmediately followed by dropwise addition of 1.54 ml of acetic acid
  5. temperatureto warm to room temperature
  6. customThe volatiles were removed under vacuum
  7. extractionthe residue was extracted from aqueous sodium bicarbonate with ethyl acetate
  8. dry with materialThe combined organic layers were dried with sodium sulfate
  9. customthe volatiles were removed
  10. customThe residue was purified by column chromatography on silica (LPS-1) (loading with 2% methanol/dichloromethane
  11. washeluting with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-a5e5a39da5a64d26bff0345ab6c1df01
Source dataset
uspto-grants-1986_03
Patent number
US04576749

Reaction notes

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