Pyrrolidine → HCID 85787464, compound

HRID 880513Notes

Reaction equation

HRID 880513 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[CH3:16].[CH3:17]OC(OC)N(C)C>>[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[CH:16]=[CH:17][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 31268PyrrolidineHCID 698542-Fluoro-6-nitrotolueneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 85787464HCID 85787464, compoundYield 80%

Procedure

Pyrrolidine (0.26 mL, 3.22 mmol) was added to a solution of 2-fluoro-6-nitrotoluene (5 g, 32.23 mmol) in N,N-dimethyl formamide dimethyl acetal (50 mL) and refluxed for 48 h. The resulting mixture was cooled to ambient temperature and partitioned between ethyl acetate (150 mL) and water (150 mL). The organic layer was separated and the aqueous layer extracted with ethyl acetate (5×30 mL). The combined organic layers were washed with water (3×30 mL), brine (3×20 mL), dried over anhydrous sodium sulphate and concentrated in vacuo to give 1-[2-(2-fluoro-6-nitro-phenyl)vinyl]pyrrolidine (6.08 g, 80%) as brown liquid.

Workup

  1. temperaturerefluxed for 48 h
  2. custompartitioned between ethyl acetate (150 mL) and water (150 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with ethyl acetate (5×30 mL)
  5. washThe combined organic layers were washed with water (3×30 mL), brine (3×20 mL)
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6219f9f5c9d2405ab3fd08027158017d
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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