Potassium Iodide → 3-{1-(Cyclopropylmethyl)-4-piperidinyl}-1,2-benzisothiazole hydrobromide

HRID 1248402Notes

Reaction equation

HRID 1248402 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.[CH:16]1([CH2:19]Cl)[CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[BrH:29].CCOCC>CCOCC.O.CN(C)C=O>[BrH:29].[CH:16]1([CH2:19][N:1]2[CH2:2][CH2:3][CH:4]([C:7]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[S:9][N:8]=3)[CH2:5][CH2:6]2)[CH2:18][CH2:17]1

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 80013(Chloromethyl)cyclopropaneHCID 133240934-(3-Benzisothiazolyl) piperidineHCID 86739792Ether hydrobromide

Product 1

HCID 202557543-{1-(Cyclopropylmethyl)-4-piperidinyl}-1,2-benzisothiazole hydrobromideYield 25%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 5.0 g of 3-(4-piperidinyl)-1,2-benzisothiazole, 2.30 g of cyclopropylmethyl chloride, 7.95 g of potassium carbonate, 0.25 g of potassium iodide and 90 ml of dimethylformamide was heated at 90° for 20 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate and the solvent was removed in vacuo to yield an oil. The oil was dissolved in ether and saturated hydrogen bromide/ether solution was added dropwise to precipitate the salt. The salt was recrystallized two times from ethyl acetate/ethanol to yield 2.0 g (25%) of product, mp 214°-216°.

Workup

  1. temperaturewas heated at 90° for 20 hrs
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customto yield an oil
  7. customto precipitate the salt
  8. customThe salt was recrystallized two times from ethyl acetate/ethanol

Sources & evidence

ORD record
ord-0d7b6b4ab3ef469f896c583ccb057d7a
Source dataset
uspto-grants-1985_06
Patent number
US04524074

Reaction notes

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