Pyrrolidine → HCID 67220588, compound

HRID 1258475Notes

Reaction equation

HRID 1258475 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH3:10].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>CCCCCC.[Ti](Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)=[CH2:10]

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 677702,4-Difluoroacetophenone

Product 1

HCID 67220588HCID 67220588, compoundYield 36.6%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 8058HexaneSolvent

Procedure

To a solution of 1-(2,4-difluorophenyl)ethanone (10.0 g, 64.0 mmol) and pyrrolidine (32.1 mL, 384 mmol) in hexane (150 mL) was added titanium tetrachloride (3.86 mL, 35.2 mmol) dropwise at 0° C. over 15 minutes. The reaction mixture was stirred at room temperature for 24 hours and filtered. The filtrate was evaporated in vacuo to give pale yellow oil, which was distilled under reduced pressure (0.3 mmHg, 90-120° C.) to give the title compound as a pale yellow oil (4.90 g, 36%).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated in vacuo
  3. customto give pale yellow oil, which
  4. distillationwas distilled under reduced pressure (0.3 mmHg, 90-120° C.)

Sources & evidence

ORD record
ord-a54ef22afc524a059fbc6509d0681a18
Source dataset
uspto-grants-2013_06
Patent number
US08466166B2

Reaction notes

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