Aminoacetaldehyde dimethyl acetal → 2,2-Dimethoxy-N-(2-oxo-2-((2-phenylethyl)amino)ethyl)ethanaminium chloride

HRID 1045646

Reaction equation

HRID 1045646 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].[Cl:8][CH2:9][C:10]([NH:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11]>C1(C)C=CC=CC=1>[ClH:8].[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH:5][CH2:9][C:10]([NH:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11]

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 949212-Chloro-N-phenethyl-acetamide

Product 1

HCID 462240062,2-Dimethoxy-N-(2-oxo-2-((2-phenylethyl)amino)ethyl)ethanaminium chlorideYield 52%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Aminoacetaldehyde dimethylacetal (20.05 g, 191 mmol) was added to the solution of 2-chloro-N-phenethyl-acetamide (18.33 g, 92.7 mmol) in toluene (92 ml) and refluxed in 2 hours. After ice-cooling and removal of precipitate by filtration, filtrate was washed with water and dried with magnesium sulfate. The solvents were removed under reduced pressure, and 4N hydrogen chloride in ethyl acetate (18 ml) was added to the residue followed by filtration and wash with ethyl acetate and diethyl ether afforded 2-(2,2-dimethoxy-ethylamino)-N-phenethyl-acetamide hydrochloride (8.77 g, 52%).

Workup

  1. temperaturerefluxed in 2 hours
  2. temperatureAfter ice-cooling
  3. customremoval of precipitate
  4. filtrationby filtration, filtrate
  5. washwas washed with water
  6. dry with materialdried with magnesium sulfate
  7. customThe solvents were removed under reduced pressure, and 4N hydrogen chloride in ethyl acetate (18 ml)
  8. additionwas added to the residue
  9. filtrationfollowed by filtration
  10. washwash with ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-da5f6fad7a7d4445a6d43a7e62205ae6
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Linked notes

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