Acetic Anhydride → HCID 57634654, compound
Reaction equation
[CH3:1][CH:2]1[CH2:4][N:3]1[CH2:5][C:6]([O:8]CC)=O.[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH2:17])=[CH:14][CH:13]=1.B(F)(F)F.[CH3:24][CH2:25][O:26]CC.C(N(CC)CC)C.C(OC(=O)C)(=O)C>ClCCl>[C:25]([N:3]1[CH:2]([CH3:1])[CH2:4][N:17]([CH2:16][C:15]2[CH:18]=[CH:19][C:12]([F:11])=[CH:13][CH:14]=2)[C:6](=[O:8])[CH2:5]1)(=[O:26])[CH3:24]Participants
Conditions
- Temperature
- 0 °C
Procedure
A mixture of ethyl (2-methylaziridin-1-yl)acetate (4.0 g, 28 mmol), 4-fluorobenzylamine (5.3 g, 42 mmol), and boron trifluoride etherate (0.5 mL) was heated in a sealed stainless steel vessel inside a Teflon liner at 95° C. for 60 h (Bull. Chem. Soc. Jpn. 1986, 59: 321). The resulting mixture was dissolved in dichloromethane (50 mL), cooled to 0° C., and treated with a mixture of triethylamine (13 mL, 95 mmol) and acetic anhydride (6.7 mL, 71 mmol). The reaction mixture was stirred at room temperature overnight, and extracted successively with saturated aqueous solution of sodium bicarbonate, dilute aqueous HCl, and brine. The organic extract was dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a mixture of 7-10 % methanol in ethyl acetate. Collection and concentration of appropriate fractions provided the title piperazinone.
Workup
- extractionextracted successively with saturated aqueous solution of sodium bicarbonate, dilute aqueous HCl, and brine
- extractionThe organic extract
- dry with materialwas dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
- additionThe residue was subjected to column chromatography on silica gel eluting with a mixture of 7-10 % methanol in ethyl acetate
- customCollection and concentration of appropriate fractions
Sources & evidence
- ORD record
- ord-abe30dfe3e35488ea91d21589c8c47a3
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07517532B2
Reaction notes
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