Dimethylformamide → 1-[2-(5-Nitro-2-pentafluoroethylphenoxy)-ethyl]-pyrrolidine

HRID 888079Notes

Reaction equation

HRID 888079 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])=[C:8]([OH:10])[CH:9]=1)([O-:3])=[O:2].Cl.Cl[CH2:20][CH2:21][N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:11]([F:16])([F:17])[C:12]([F:13])([F:14])[F:15])=[C:8]([CH:9]=1)[O:10][CH2:20][CH2:21][N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 17756181Phenol, 5-nitro-2-(1,1,2,2,2-pentafluoroethyl)-

Product 1

HCID 865946891-[2-(5-Nitro-2-pentafluoroethylphenoxy)-ethyl]-pyrrolidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A flask was charged with 5-nitro-2-pentafluoroethylphenol (3.67 g, 14.2 mmol), 1-(2-chloroethyl)pyrrolidine hydrochloride (9.71 g, 57.1 mmol), DMF (20 mL) and combined with K2CO3 (5.9 g, 42.1 mmol) and heated to 70° C. for 24 h. The reaction was cooled to RT, taken up in to EtOAc and washed with 2N NaOH, and brine. The organic layer was dried with MgSO4, filtered and concentrated in vacuo. The aqueous layer was acidified, extracted with EtOAc and dried with MgSO4, filtered, concentrated in vacuo and combined with the other portion. The title compound was purified by column chromatography using 0-10% MeOH in CH2Cl2.

Workup

  1. temperatureThe reaction was cooled to RT
  2. washwashed with 2N NaOH, and brine
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. extractionextracted with EtOAc
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe title compound was purified by column chromatography

Sources & evidence

ORD record
ord-74d96a00683d4c3086922e478de404f8
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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