Dimethylformamide → N,N-diethyl-2-[4-(2-fluoro-4-nitro-phenyl)piperazin-1-yl]-2-phenyl-acetamide

HRID 2196178Notes

Reaction equation

HRID 2196178 reaction equation
CN(C=O)C.[F:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C([O-])([O-])=O.[K+].[K+].Br[CH:29]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:30]([N:32]([CH2:35][CH3:36])[CH2:33][CH3:34])=[O:31]>CC(OC)(C)C>[CH2:35]([N:32]([CH2:33][CH3:34])[C:30](=[O:31])[CH:29]([N:19]1[CH2:20][CH2:21][N:16]([C:8]2[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:7]=2[F:6])[CH2:17][CH2:18]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH3:36]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27830661-(2-fluoro-4-nitrophenyl)piperazineHCID 14897375HCID 14897375, compound

Product 1

HCID 58157308N,N-diethyl-2-[4-(2-fluoro-4-nitro-phenyl)piperazin-1-yl]-2-phenyl-acetamide

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A 500 mL, round-bottomed flask under a positive pressure of nitrogen was equipped with a magnetic stirrer and charged with anhydrous DMF (100 mL), 1-(2-fluoro-4-nitro-phenyl)-piperazine (4.0 g, 17.8 mmol), anhydrous K2CO3 (4.9 g, 35.5 mmol) and 2-bromo-N,N-diethyl-2-phenyl-acetamide (6.2 g, 23.0 mmol). The pale yellow reaction mixture was stirred at ambient temperature for 4 h, following which the solvent was removed on the rotary evaporator to yield a yellow colored semi-solid. MTBE (250 mL) was added and the resulting suspension was stirred at ambient temperature for 0.5 h and then filtered. The filtrate was extracted with 1.5N HCl (1×200 mL, then 1×100 mL). The aqueous layers were pooled, cooled to ˜0° C. in an ice bath and then basified with 2N NaOH (to pH ca. 13). The basified reaction mixture was extracted with MTBE (4×125 mL). The organic layers were pooled, dried over anhydrous sodium sulfate, filtered and concentrated to yield a brown colored oil. The oil was purified by silica gel chromatography (solvent: EtOAc/Hexane) to yield the title compound as a reddish-brown oil.

Workup

  1. customA 500 mL, round-bottomed flask under a positive pressure of nitrogen was equipped with a magnetic stirrer
  2. customwas removed on the rotary evaporator
  3. customto yield a yellow colored semi-solid
  4. stirringthe resulting suspension was stirred at ambient temperature for 0.5 h
  5. filtrationfiltered
  6. extractionThe filtrate was extracted with 1.5N HCl (1×200 mL
  7. temperaturecooled to ˜0° C. in an ice bath
  8. customThe basified reaction mixture
  9. extractionwas extracted with MTBE (4×125 mL)
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customto yield a brown colored oil
  14. customThe oil was purified by silica gel chromatography (solvent: EtOAc/Hexane)

Sources & evidence

ORD record
ord-ea16eaf4abc048ab9a5951a514b38586
Source dataset
uspto-grants-2012_12
Patent number
US08338426B2

Reaction notes

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