Ethylenediamine → N,N-Bis-Carbobenzyloxyethylenediamine

HRID 1883298Notes

Reaction equation

HRID 1883298 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH2:12]([NH2:15])[CH2:13][NH2:14].[OH-:16].[Na+]>>[C:2]([N:14]([C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:16])[CH2:13][CH2:12][NH2:15])([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3]

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 23510767N,N-Bis-Carbobenzyloxyethylenediamine

Procedure

Benzyl chloroformate (40 mL, 280 mmol) was added dropwise over 45 min to a vigorously stirred solution of ethylenediamine (9.4 mL, 0.5 equiv) in 1M NaOH (310 mL, 1 equiv) at 0° C. A heavy white precipitate formed and the mixture was stirred for 4 h following addition. The resulting solid product was collected by filtration, washed with water and then hexane, and then air-dried overnight (46.17 g, 100%). 1H-NMR (CDCl3) δ 3.32 (s, 4H), 5.10 (s, 4H), 5.23 (br, 2H), 7.35 (s, 10HS MS (ESI) 329.3 (MH)+.

Workup

  1. customA heavy white precipitate formed
  2. additionaddition
  3. filtrationThe resulting solid product was collected by filtration
  4. washwashed with water
  5. dry with materialhexane, and then air-dried overnight (46.17 g, 100%)

Sources & evidence

ORD record
ord-a2a0237d920f4601b0a28b2c68e5d757
Source dataset
uspto-grants-2004_07
Patent number
US06759509B1

Reaction notes

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