Hydrochloric Acid → Benzyl N-(2-aminoethyl)carbamate hydrochloride

HRID 1883299Notes

Reaction equation

HRID 1883299 reaction equation
[C:1]([N:11](C(OCC1C=CC=CC=1)=O)[CH2:12][CH2:13][NH2:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[ClH:25]>C(O)(=O)C>[ClH:25].[C:1]([NH:11][CH2:12][CH2:13][NH2:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23510767N,N-Bis-Carbobenzyloxyethylenediamine

Product 1

HCID 12715871Benzyl N-(2-aminoethyl)carbamate hydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N,N-Bis-Carbobenzyloxyethylenediamine 11 (23.91 g, 72.8 mmol) in glacial acetic acid (100 mL) was treated with 12M HCl (12.1 mL, 2 equiv). The stirred mixture was heated at reflux for 1 h and then left to stand at rt overnight. A small amount of solid was removed by filtration and the filtrate was diluted with ether (700 mL) and left to stand at rt for 2 h. The resulting white solid product was collected by filtration, washed repeatedly with ether, and dried in a vacuum dessicator overnight (9.2440 g, 55%). 1H-NMR (DMSO-d6) δ 2.87 (t, 2H), 3.30 (q, 2H), 5.04 (s, 2H), 7.33 (m, 5H), 7.49 (brt, 1H), 8.22 (br, 3H).

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureat reflux for 1 h
  3. waitleft
  4. customA small amount of solid was removed by filtration
  5. additionthe filtrate was diluted with ether (700 mL)
  6. waitleft
  7. waitto stand at rt for 2 h
  8. filtrationThe resulting white solid product was collected by filtration
  9. washwashed repeatedly with ether
  10. customdried in a vacuum dessicator overnight (9.2440 g, 55%)

Sources & evidence

ORD record
ord-a8f8fae6073e41fb8fa29574600c17f1
Source dataset
uspto-grants-2004_07
Patent number
US06759509B1

Reaction notes

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