2,6-Lutidine → HCID 80700116, compound

HRID 1753953Notes

Reaction equation

HRID 1753953 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].S(C1C=CC(C)=CC=1)(O[CH2:13][CH2:14][F:15])(=O)=O.N1C(C)=CC=CC=1C>CN(C=O)C.C(OCC)(=O)C>[F:15][CH2:14][CH2:13][NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([F:1])[CH:3]=1

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 97423-FluoroanilineHCID 2560192-Fluoroethyl p-Toluenesulfonate

Product 1

HCID 80700116HCID 80700116, compoundYield 10.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Fluoroaniline (1.4 g, 11.6 mmol, 1.2 mL) and 2-fluoroethyl tosylate (12; prepared according to Example 2(a)) (2.5 g, 11.6 mmol) and lutidine (1.24 g, 11.6 mmol) were stirred and heated in DMF (5 mL) at 100° C. overnight. The reaction was allowed to cool and then diluted with ethyl acetate (100 mL). This was washed with, water (3×40 mL) and the organics were dried and concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with petrol (A) and ethyl acetate (B) (10% B, 100 g, 12 CV, 60 mL/min) to afford 184 mg (10%) of (2-fluoro-ethyl)-(3-fluoro-phenyl)-amine (43) as a yellow oil. The structure was confirmed by 1H NMR (300 MHz, CDCl3) δH 3.37 (1H, q, J=6 Hz, NCH2CH2F), 3.46 (1H, q, J=6 Hz, NCH2CH2F), 4.12 (1H, s, br, NH), 4.54 (1H, t, J=3 Hz, NCH2CH2F), 4.69 (1H, t, J=3 Hz, NCH2CH2F), 6.31-6.50 (3H, m, NCCHCHCH), 7.10-7.25 (1H, m, NCCHCF).

Workup

  1. temperatureto cool
  2. washThis was washed with, water (3×40 mL)
  3. customthe organics were dried
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by silica gel chromatography
  6. washeluting with petrol (A) and ethyl acetate (B) (10% B, 100 g, 12 CV, 60 mL/min)

Sources & evidence

ORD record
ord-c4b78e28b85e41ba9bbf5155dfc56665
Source dataset
uspto-grants-2015_10
Patent number
US09168317B2

Reaction notes

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