1-(2-Fluorophenyl)piperazine → HCID 10064035, compound

HRID 1768366Notes

Reaction equation

HRID 1768366 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C(O[BH-](O[C:24](=[O:26])[CH3:25])OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.ClCCl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:6][C:5]2[O:26][C:24]3[C:25](=[N:8][CH:3]=[CH:2][CH:7]=3)[CH:4]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 705291-(2-Fluorophenyl)piperazineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 10064035HCID 10064035, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent2×

Procedure

1-(2-Fluorophenyl)piperazine (0.18 g, 1.0 mmol) and sodium triacetoxyborohydride (0.32 g, 1.5 mmol) in dichloroethane (2 mL) were treated with the product from Example 35B (2 mL, 1.0 mmol) as a 0.5M solution in dichloroethane dropwise. The mixture was allowed to stir at room temperature for 17 hours. The mixture was diluted with dichloromethane (10 mL) and washed with 1N NaOH. The organic layer was dried over magnesium sulfate, filtered, and the filt0rate concentrated under reduced pressure. The residue was purified by flash chromatography on silica (dichloromethane to 2% methanol in dichloromethane) to provide the title compound. 1H NMR (CDCl3, 400 MHz) δ 2.81 (br, 4H), 3.19 (br, 4H), 3.85 (s, 2H), 6.89 (s, 1H), 7.00 (m, 4H), 7.20 (dd, J=4.75, 8.14 Hz, 1H), 7.74 (d, J=8.48 Hz, 1H), 8.52 (d, J=4.75 Hz 1H); MS (DCI/NH3) m/z 312.2 (M+H)+; Anal. Calcd for C18H18FN3O: C, 69.44; H, 5.83; N, 13.50. Found: C, 69.36; H, 5.59; N, 13.28.

Workup

  1. washwashed with 1N NaOH
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filt0rate concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica (dichloromethane to 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-266425e9bbb74b81b11e66acffd279be
Source dataset
uspto-grants-2007_06
Patent number
US07235661B2

Reaction notes

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