Potassium Iodide → HCID 12919832, compound

HRID 851115Notes

Reaction equation

HRID 851115 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8](=[O:9])[C:6]1=[O:7].[CH:16]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[I-].[K+].C(=O)(O)[O-].[Na+]>CN(C)C=O.C(N(CC)CC)C>[ClH:1].[ClH:1].[CH:16]([N:29]1[CH2:34][CH2:33][N:32]([CH2:2][CH2:3][CH2:4][N:5]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:8](=[O:9])[C:6]2=[O:7])[CH2:31][CH2:30]1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 70048BenzhydrylpiperazineHCID 516892Sodium BicarbonateHCID 11085431HCID 11085431, compound

Product 1

HCID 12919832HCID 12919832, compoundYield 131%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 1-(3-chloropropyl)isatin (13.44 g), 1-benzhydrylpiperazine (19.92 g), triethylamine (7.2 g) and potassium iodide (9.96 g) in N,N-dimethylformamide (144 ml) was stirred for 1.5 hours at 80° to 85° C. The reaction mixture was cooled, poured into a cold aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated. The residue was dissolved in chloroform and subjected to column chromatography on silica gel (60 g) using chloroform as an eluent. The eluate was evaporated, and the remaining oil was dissolved in ethanol (160 ml). To a solution was added 29% ethanolic hydrogen chloride (30 ml) under cooling or an ice bath, and the resultant mixture was stirred for 10 minutes. The precipirated crystals were collected by filtration and then dried to give 1-[3-(4-benzhydryl-1-piperazinyl)propyl]isatin dihydrochloride (20.17 g). Thus obtained product was purified by recrystallization from 92% ethanol (410 ml) to give the purified product of the same compound (10.44 g), mp. 245° to 248° C. (dec.).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. dissolutionThe residue was dissolved in chloroform
  7. customThe eluate was evaporated
  8. dissolutionthe remaining oil was dissolved in ethanol (160 ml)
  9. additionTo a solution was added 29% ethanolic hydrogen chloride (30 ml)
  10. temperatureunder cooling
  11. stirringan ice bath, and the resultant mixture was stirred for 10 minutes
  12. filtrationThe precipirated crystals were collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-6207fd64a4dd4854bd2926ba67c5385f
Source dataset
uspto-grants-1983_05
Patent number
US04382934

Reaction notes

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