Triethylamine → HCID 28431408, compound

HRID 1162820Notes

Reaction equation

HRID 1162820 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].C(N(CC)CC)C.[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1>C1COCC1>[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH:20][CH2:2][C:3]([O:5][CH3:6])=[O:4])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 673264-Fluorobenzylamine

Product 1

HCID 28431408HCID 28431408, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl bromoacetate (24.0 mL, 254 mmol) in anhydrous THF (264 mL) was added dropwise triethylamine (35.3 mL, 254 mmol). The cloudy mixture was treated rapidly with 4-fluorobenzylamine, and the resulting viscous mixture was stirred at ambient temperature under inert atmosphere for 18 h. THF was removed in vacuo, and the resulting residue was suspended in diethyl ether. The mixture was filtered and the solids washed with excess diethyl ether. Concentration of the filtrate in vacuo afforded the title compound as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.31-7.27 (m, 2H), 7.04-6.99 (m, 2H), 3.77 (s, 2H), 3.74 (s, 3H), 3.41 (s, 2H), 1.82 (br s, 1H).

Workup

  1. customTHF was removed in vacuo
  2. filtrationThe mixture was filtered
  3. washthe solids washed with excess diethyl ether

Sources & evidence

ORD record
ord-3f6eee5b695e40fa858385d260ee376a
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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