3-Fluoropyridine → HCID 18321141, compound

HRID 1782715Notes

Reaction equation

HRID 1782715 reaction equation
F[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[C:8]1([CH2:14][N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1([Li])C=CC=CC=1.C1CCCCC1.C(OCC)C>C(OCC)C>[C:8]1([CH2:14][N:15]2[CH2:16][CH2:17][NH:18][CH:19]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=3)[CH2:20]2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 677943-FluoropyridineHCID 759941-BenzylpiperazineHCID 21895417Cyclohexane diethyletherHCID 178506676HCID 178506676, compound

Product 1

HCID 18321141HCID 18321141, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5.0 g (0.0515 mol) of 3-fluoropyridine and 43.5 ml of 1-(phenylmethyl)piperazine in 300 ml of anhydrous diethylether was added dropwise, at boiling temperature, within 2.5 hours, 56 ml (0.112 mol) of a 2 molar solution of phenyl-lithium in a cyclohexane-diethylether mixture (7/3 v/v) and the resulting mixture was then kept at reflux temperature for a further 4 hours. The crude reaction product obtained as an oil after working up in the usual way was purified by column chromatography over silica gel (30-60 μm) using FM1/cyclohexane (7/3 v/v) as eluant. 12.0 g (92% of theory) of a colourless oil were obtained, Rf 0.52 (FM4; Macherey-Nagel, POLYGRAM® SIL G/UV254 Pre-coated plastic sheets for TLC).

Workup

  1. temperatureat reflux temperature for a further 4 hours
  2. customThe crude reaction product
  3. customobtained as an oil
  4. customwas purified by column chromatography over silica gel (30-60 μm)
  5. custom12.0 g (92% of theory) of a colourless oil were obtained

Sources & evidence

ORD record
ord-bc115b73d8254c46b155ef5962d23ab0
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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