Potassium Iodide → [2-Benzothiazolyl][1-(2-phenylethyl)-4-piperidinyl]methanone

HRID 1491681Notes

Reaction equation

HRID 1491681 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11].C(C(O)=O)(F)(F)F.[C:25]1([CH2:31][CH2:32]Br)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:32][CH2:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:14][CH2:13]1)=[O:11]

Participants

9

Reactant 6

HCID 4875Potassium IodideHCID 6422Trifluoroacetic acidHCID 7666Phenethyl bromide3×HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 152370094-(Benzthiazole-2-carbonyl)piperidine

Product 1

HCID 15337460[2-Benzothiazolyl][1-(2-phenylethyl)-4-piperidinyl]methanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Mix (2-benzothiazolyl)(4-piperidinyl)methanone.CF3CO2H (2.56 g, 7.13 mmol), 2-phenylethyl bromide (1.45 g, 7.84 mmol), 18-Crown-6 (188 mg, 0.71 mmol), potassium carbonate (9.85 g, 71.3 mmol) and methylene chloride (100 mL). Stir at room temperature under an argon atmosphere for 2 hours, then add potassium iodide (200 mg). Stir at room temperature for an additional 2 hours then heat a t reflux overnight. Add additional 2-phenylethyl bromide (1.45 g, 7.84 mmol) and heat at reflux overnight. Add additional 2-phenylethyl bromide (1.45 g, 7.84 mmol) and heat at reflux overnight. Cool the reaction to room temperature and pour into water (150 mL). Separate the organic phase, wash with water (100 mL) and dry (Na2SO4). Evaporate the solvent in vacuo and purify by chromatography (20% ethyl acetate/hexane with 2% triethylamine) to give the title compound as a yellow solid; mp 108.5°-109.5° C.

Workup

  1. stirringStir at room temperature for an additional 2 hours
  2. temperaturethen heat a t
  3. temperaturereflux overnight
  4. temperatureheat
  5. temperatureat reflux overnight
  6. temperatureheat
  7. temperatureat reflux overnight
  8. temperatureCool
  9. customthe reaction to room temperature
  10. customSeparate the organic phase
  11. washwash with water (100 mL)
  12. dry with materialdry (Na2SO4)
  13. customEvaporate the solvent in vacuo
  14. custompurify by chromatography (20% ethyl acetate/hexane with 2% triethylamine)

Sources & evidence

ORD record
ord-f964c64b5dbd48d8a5cff4fa9cbbcd79
Source dataset
uspto-grants-1994_12
Patent number
US05371093

Reaction notes

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