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

HRID 10461Notes

Reaction equation

HRID 10461 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-1eb4ad4101bd408cab4df1eea911d020
Source dataset
uspto-grants-2006_08
Patent number
US07094769B2

Reaction notes

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