Triethylamine → Benzyl 2-[({[2-(diisopropylamino)ethyl]amino}carbonyl)amino]ethylcarbamate

HRID 353639Notes

Reaction equation

HRID 353639 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH:16]([N:19]([CH:30]([CH3:32])[CH3:31])[CH2:20][CH2:21][NH:22][C:23](N1C=CN=C1)=[O:24])([CH3:18])[CH3:17].C(N(CC)CC)C>ClCCl>[CH:30]([N:19]([CH:16]([CH3:18])[CH3:17])[CH2:20][CH2:21][NH:22][C:23]([NH:2][CH2:3][CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:24])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12715871Benzyl N-(2-aminoethyl)carbamate hydrochlorideHCID 21978296N-[2-(diisopropylamino)ethyl]-1H-imidazole-1-carboxamide

Product 1

HCID 21978301Benzyl 2-[({[2-(diisopropylamino)ethyl]amino}carbonyl)amino]ethylcarbamateYield 109.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzyl 2-aminoethylcarbamate hydrochloride (4.33 g, 18.8 mmol), N-[2-(diisopropylamino)ethyl]-1H-imidazole-1-carboxamide (Preparation 19) (3.73 g, 15.64 mmol) and triethylamine (2.62 ml, 18.8 mmol) in dichloromethane (100 ml) was heated under reflux for 14 hours. The solution was allowed to cool to room temperature and then washed with water (20 ml). The aqueous layer was separated and extracted with more dichloromethane (20 ml). The combined organic layers were dried over anhydrous magnesium sulfate and solvent evaporated under reduced pressure to give the title compound as a yellow oil (6.25 g).

Workup

  1. temperatureunder reflux for 14 hours
  2. washwashed with water (20 ml)
  3. customThe aqueous layer was separated
  4. extractionextracted with more dichloromethane (20 ml)
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate and solvent
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fd09094a1e5f459c91921fc8190f3e90
Source dataset
uspto-grants-2004_06
Patent number
US06753322B2

Reaction notes

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