Triethylamine → HCID 22620025, compound

HRID 840588Notes

Reaction equation

HRID 840588 reaction equation
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][C:8](CN)=[CH:7][CH:6]=1)([O-:4])=[O:3].[CH2:13]([N:15](CC)CC)C.[C:20]([O:24][C:25]([O:27]C(OC(C)(C)C)=O)=O)([CH3:23])([CH3:22])[CH3:21]>ClCCl>[C:20]([O:24][C:25]([NH:15][CH2:13][C:11]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:2]([O-:4])=[O:3])[CH:12]=1)=[O:27])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 112524674-Nitrobenzylamine hydrochloride

Product 1

HCID 22620025HCID 22620025, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-nitrobenzylamine hydrochloride (10.3 g, 54.7 mmol) and triethylamine (11.1 g, 109 mmol) in dichloromethane (75 mL) was added a solution of di-tert-butyldicarbonate (15.5 g, 71.1 mmol) in dichloromethane (25 L). After stirring overnight at room temperature, the reaction was washed with 10k citric acid (2×250 mL), dried over magnesium sulfate, filtered, and the solvent removed under reduced pressure. The residue was recrystallized from ethyl acetate/hexanes to afford the 13.80 g of the title compound. (100%).

Workup

  1. washthe reaction was washed with 10k citric acid (2×250 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-fca31947cbfc4afeb051df27f6b233b5
Source dataset
uspto-grants-2002_04
Patent number
US06369070B1

Reaction notes

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