Ethylenediamine → N-BOC-ethylenediamine

HRID 356799Notes

Reaction equation

HRID 356799 reaction equation
[C:1](OC([O-])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:12]([NH2:15])[CH2:13][NH2:14]>O1CCOCC1>[C:4]([O:3][C:1]([NH:14][CH2:13][CH2:12][NH2:15])=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 22064466Tert-butyldicarbonate

Product 1

HCID 187201N-BOC-ethylenediamine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

This compound was prepared as described previously (Krapcho et al., 1990, Synthetic Commun. 20: 2559-2564). Briefly, a solution of tert.butyl dicarbonate (5.0 g, 0.023 mol) in dioxane (50 ml) was slowly added to ethylenediamine (11.0 ml, 0.165 mol) in dioxane (60 ml). After 24 hrs of stirring the solvent was evaporated and the residue was dissolved in water (80 ml), insoluble byproduct was filtered off and the filtrate was extracted with dichloromethane (3×100 ml). After evaporation of the solvent the product was crystallized from solvent mixture of diethylether--petroleum ether or ethyl acetate--petroleum ether. Yield 2.6 g (71%). NMR (300 MHz, DMSO-d6, 25° C.) d: 1.39 (s, 9H, tBu), 2.83 (m, 2H, Ca H2), 3.16 (q, 2H, CbH2), 6.93 (t, 1H, NH), 7.77 (br, 2H, NH2). M.p. 75° C.

Workup

  1. customThis compound was prepared
  2. customwas evaporated
  3. dissolutionthe residue was dissolved in water (80 ml)
  4. filtrationinsoluble byproduct was filtered off
  5. extractionthe filtrate was extracted with dichloromethane (3×100 ml)
  6. customAfter evaporation of the solvent the product
  7. customwas crystallized from solvent mixture of diethylether

Sources & evidence

ORD record
ord-e2519b6ad7a34918b857e05ead8aaa7b
Source dataset
uspto-grants-1998_11
Patent number
US05840485

Reaction notes

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