1,2-Ethanediamine, N1,N1-bis(1-methylethyl)- → HCID 86748144, compound

HRID 2226440Notes

Reaction equation

HRID 2226440 reaction equation
[CH:1]([N:4]([CH:8]([CH3:10])[CH3:9])[CH2:5][CH2:6][NH2:7])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:18]([O:25]C(Cl)=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:29]([O-])([O-])=[O:30].[K+].[K+]>C(Cl)Cl.CCOCC>[CH:1]([N:4]([CH:8]([CH3:10])[CH3:9])[C:5](=[C:29]=[O:30])[CH2:6][NH:7][O:25][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 84591,2-Ethanediamine, N1,N1-bis(1-methylethyl)-HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 11430Potassium Carbonate

Product 1

HCID 86748144HCID 86748144, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N,N-Diisopropyl-ethylenediamine (4.94 gm, 0.034 mol) was dissolved in CH2Cl2 (20 mL) and cooled to 0° C. under nitrogen. Triethylamine (4.7 mL) and benzyloxycarbonyl chloride (4.9 mL) were then added and the mixture was stirred overnight while being allowed to reach room temperature. The mixture was then poured into Et2O (250 mL) and K2CO3 was added. This mixture was then washed successively with H2O and brine and the pooled aqueous layers were back-extracted with Et2O. The pooled organic layers were dried over Na2SO4, filtered and evaporated to dryness. This crude reaction product was then purified on a silica gel column using initially EtOAc/hexane (1:1) as eluent followed by MeOH/EtOAc (3:7) containing 2% Et3N to afford 2.9 gm of the title compound suitable for use in the next step.

Workup

  1. customto reach room temperature
  2. additionwas added
  3. washThis mixture was then washed successively with H2O and brine
  4. extractionthe pooled aqueous layers were back-extracted with Et2O
  5. dry with materialThe pooled organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThis crude reaction product
  9. customwas then purified on a silica gel column
  10. additioncontaining 2% Et3N

Sources & evidence

ORD record
ord-61cd80437f27453ebe5bbffeea686825
Source dataset
uspto-grants-1994_09
Patent number
US05348953

Reaction notes

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