N,N-Diethylethylenediamine → HCID 59296238, compound

HRID 556717Notes

Reaction equation

HRID 556717 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].[CH3:9][O:10][CH:11]([O:14][CH3:15])[CH:12]=O>CO.[Pd]>[CH3:9][O:10][CH:11]([O:14][CH3:15])[CH2:12][NH:6][CH2:5][CH2:4][N:3]([CH2:7][CH3:8])[CH2:1][CH3:2]

Participants

5

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 162650Acetaldehyde, 2,2-dimethoxy-

Product 1

HCID 59296238HCID 59296238, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
15 °C

Procedure

A solution of N,N-diethyl-ethylenediamine (150 g) in methanol (500 mL) was treated dropwise rapidly with glyoxal dimethylacetal (60 wt % soln. in water, 225 g) at 10-15° C. After the addition was complete the solution was warmed to 15° C., then to 22° C. and left at this temperature for 16 hours. The reaction mixture was treated with 5% palladium on carbon (Johnson-Matthey type 38H paste, 15 g) and hydrogenated at 6 bar until the reaction was complete as judged by GC/MS. The catalyst was removed by filtration and the filtrate evaporated to dryness (toluene azeotrope, 2.5 L), affording 196.2 g of the sub-titled compound.

Workup

  1. additionAfter the addition
  2. customThe catalyst was removed by filtration
  3. customthe filtrate evaporated to dryness (toluene azeotrope, 2.5 L)

Sources & evidence

ORD record
ord-99183394b4b64ca98e3145e900622a01
Source dataset
uspto-grants-2011_11
Patent number
US08058294B2

Reaction notes

Loading…