Potassium Iodide → HCID 20344089, compound

HRID 2049682Notes

Reaction equation

HRID 2049682 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:33]=[CH:32][C:16]2[S:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3([C:30](=[O:31])[C:15]=2[CH:14]=1)[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3.C(=O)(O)[O-].[Na+].[I-].[K+]>CN(C)C=O.O>[Cl:12][C:13]1[CH:33]=[CH:32][C:16]2[S:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3([C:30](=[O:31])[C:15]=2[CH:14]=1)[CH2:25][CH2:26][N:27]([CH2:10][CH2:9][CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:28][CH2:29]3

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 68522Benzene, (3-bromopropoxy)-HCID 516892Sodium BicarbonateHCID 20344046HCID 20344046, compound

Product 1

HCID 20344089HCID 20344089, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1.6 g of 3-phenoxypropyl bromide in 10 ml of diemthylformamide is added, portionwise over a 20 minute span to a mixture, at 80° C., of 2.1 g of 2-chloro-10,11-dihydro-11-oxospiro[dibenz(b,f)thiepin-10,4'-piperidine], free base of Example 5, 2.1 g of sodium bicarbonate and 1.7 g of potassium iodide, in 15 ml of dimethylformamide. After total addition, the reaction mixture is stirred at 80°-85° C. for 16 hours. Thereafter, the mixture is cooled in an ice bath before being diluted with 75 ml of water. The diluted mixture is extracted with 40 ml of ether and both phases (organic and aqueous) are passed through filter paper. The filtered aqueous phase is extracted thrice with 40 ml portions of ether and the combined ether extracts are successively washed twice with 40 ml portions of ether and the combined ether extracts are successively washed twice with 40 ml portions of water, once with 20 ml of a saturated sodium chloride solution and dried. The residue is purified by passing through an alumina column, ether eluant, to provide 2-chloro-10,11-dihydro-11-oxo-1'-(3-phenoxypropyl)spiro[dibenz(b,f)thiepin-10,4'-piperidine].

Workup

  1. customat 80° C.
  2. additionAfter total addition
  3. temperatureThereafter, the mixture is cooled in an ice bath
  4. extractionThe diluted mixture is extracted with 40 ml of ether
  5. filtrationthrough filter paper
  6. extractionThe filtered aqueous phase is extracted thrice with 40 ml portions of ether
  7. washthe combined ether extracts are successively washed twice with 40 ml portions of ether
  8. washthe combined ether extracts are successively washed twice with 40 ml portions of water, once with 20 ml of a saturated sodium chloride solution
  9. customdried
  10. customThe residue is purified

Sources & evidence

ORD record
ord-17e42c2d680e49b4b666ed01cfb7735a
Source dataset
uspto-grants-1980_04
Patent number
US04198420

Reaction notes

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