Potassium Iodide → HCID 23315785, compound

HRID 745318Notes

Reaction equation

HRID 745318 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[Cl:11][CH2:12][CH2:13][CH2:14][C:15]1[C:19]2[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:18]=2[O:17][N:16]=1.C(=O)(O)[O-].[Na+].[I-].[K+]>CN(C)C=O>[ClH:11].[F:24][C:22]1[CH:21]=[CH:20][C:19]2[C:15]([CH2:14][CH2:13][CH2:12][N:2]3[CH2:3][CH2:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH2:1]3)=[N:16][O:17][C:18]=2[CH:23]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 70461,2,3,4-TetrahydroisoquinolineHCID 516892Sodium BicarbonateHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Product 1

HCID 23315785HCID 23315785, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 30 ml of dry dimethylformamide was added 2.13 g of 1,2,3,4-tetrahydroisoquinoline, 3.4 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 8.0 g of sodium bicarbonate, and a crystal of potassium iodide. After stirring at 100° C. for two hrs, the mixture was evaporated to an oil. The oil was stirred with 100 of ml water for five mins and then extracted with ether. The ether extract was washed with water (2×), saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the solvent was evaporated to an oil. A 4.5 g-portion of the oil was dissolved in ether and treated with ethereal hydrogen chloride, and the resultant salt was recrystallized from ethyl acetate/methanol/ether to give 3.0 g (54%) of product, mp 174°-176° C.

Workup

  1. customthe mixture was evaporated to an oil
  2. stirringThe oil was stirred with 100 of ml water for five mins
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with water (2×), saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtering
  8. customthe solvent was evaporated to an oil
  9. dissolutionA 4.5 g-portion of the oil was dissolved in ether
  10. additiontreated with ethereal hydrogen chloride
  11. customthe resultant salt was recrystallized from ethyl acetate/methanol/ether

Sources & evidence

ORD record
ord-331cfb8b2a6a4020a3e2e350b76a9794
Source dataset
uspto-grants-1986_07
Patent number
US04598152

Reaction notes

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