Water → HCID 23117128, compound

HRID 1921269Notes

Reaction equation

HRID 1921269 reaction equation
[CH:1]1([C:7]2[C:11]3[CH:12]=[CH:13][C:14]([OH:16])=[CH:15][C:10]=3[O:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.Cl[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C([O-])([O-])=O.[K+].[K+].O>CC#N>[CH:1]1([C:7]2[C:11]3[CH:12]=[CH:13][C:14]([O:16][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:15][C:10]=3[O:9][N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 135736092HCID 135736092, compound

Product 1

HCID 23117128HCID 23117128, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-cyclohexyl-1,2-benzisoxazol-6-ol (2.69 g, 12 mmol), 1-(2-chloroethyl)-piperidine hydrochloride (2.39 g, 13 mmol) and K2CO3 (3.59 g, 26 mmol) in CH3CN (30 ml) was heated at reflux for 3 h and stirred at room temperature overnight. The reaction mixture was poured into H2O and extracted with EtOAc. The organic extract was washed with brine, dried (Na2SO4) and concentrated to give a residue (3.78 g). This residue was purified by flash chromatography (toluene/1,4-dioxane 8/2). Crystallisation from EtOH gave white crystals (0.53 g, 13.4%). mp 69° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-469b1565d7874af1b88217a5cfa3396b
Source dataset
uspto-grants-2012_05
Patent number
US08173679B2

Reaction notes

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