Acetonitrile → HCID 12004312, compound

HRID 2241978Notes

Reaction equation

HRID 2241978 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH2:11][CH2:10]1.[C:21](#[N:23])[CH3:22]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]3[C:22]4[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=4[O:2][N:23]=3)[CH2:17][CH2:16]2)[CH2:13][CH2:14]1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 1530394HCID 1530394, compound

Product 1

HCID 12004312HCID 12004312, compound

Procedure

1,2-benz-isoxazole-3-trifluoromethyl sulfonate I (Step 1, 0.50 g) and 4-(4-(2-methoxyphenyl)piperazin-1-yl)piperidine (Example G, Step 2, above, 0.514 g) were added to a cold suspension of CsCO3 (0.92 g) in acetonitrile (6 mL) under vigorous stirring. The reaction mixture was stirred at room temperature for 48 hours. The mixture was then filtered and concentrated on a rotary evaporator. The residue was dissolved in water extracted with CH2Cl2, dried over anhydrous MgSO4, filtered and concentrated on a rotary evaporator. The desired product was purified by flash chromatography on silica gel using ethyl acetate/hexane to give 0.34 g as an off-white solid; MP 71-73° C.; MS (ES) m/z (relative intensity): 393 (M+H)+ (100).

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationconcentrated on a rotary evaporator
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with CH2Cl2
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated on a rotary evaporator
  8. customThe desired product was purified by flash chromatography on silica gel
  9. customto give 0.34 g as an off-white solid

Sources & evidence

ORD record
ord-15aab7ab9ee24f56934a9bf89eeee401
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

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