Potassium Iodide → 3-{1-[Phenethyl]-4-piperidinyl}-1,2-benzisothiazole hydrobromide

HRID 1248403Notes

Reaction equation

HRID 1248403 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9][N:8]=2)[CH2:3][CH2:2]1.[CH2:16]([Br:24])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CN(C)C=O>[BrH:24].[CH2:16]([N:1]1[CH2:2][CH2:3][CH:4]([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9][N:8]=2)[CH2:5][CH2:6]1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 133240934-(3-Benzisothiazolyl) piperidine

Product 1

HCID 202557573-{1-[Phenethyl]-4-piperidinyl}-1,2-benzisothiazole hydrobromide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 5.0 g of 3-(4-piperidinyl)-1,2-benzisothiazole, 4.60 g of phenethyl bromide, 7.95 g of potassium carbonate, 0.25 g of potassium iodide and 90 ml of dimethylformamide was heated at 60° for 20 hrs and stirred for 21/2 days at ambient temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic extracts were dried over anhydrous magnesium sulfate and the solvent was removed in vacuo to yield an oil. The oil was purified by elution column chromatography [silica gel (20:1); using 1% methanol in dichloromethane]. The eluate was evaporated and the residue was dissolved in ether and a saturated hydrogen bromide/ether solution was added dropwise to precipitate the salt. The salt was recrystallized from ether-ethanol 3.0 g (32%) of product, mp 233°-235°.

Workup

  1. temperaturewas heated at 60° for 20 hrs
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customto yield an oil
  6. customThe oil was purified by elution column chromatography [silica gel (20:1); using 1% methanol in dichloromethane]
  7. customThe eluate was evaporated
  8. dissolutionthe residue was dissolved in ether
  9. additiona saturated hydrogen bromide/ether solution was added dropwise
  10. customto precipitate the salt
  11. customThe salt was recrystallized from ether-ethanol 3.0 g (32%) of product, mp 233°-235°

Sources & evidence

ORD record
ord-6fadac015a034970aedf2ba66347c9cc
Source dataset
uspto-grants-1985_06
Patent number
US04524074

Reaction notes

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