Potassium Iodide → HCID 178528011, compound

HRID 722694Notes

Reaction equation

HRID 722694 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:8][C:9]1[CH:18]=[CH:17][C:12]([CH2:13][N:14]=[C:15]=[S:16])=[CH:11][CH:10]=1.Cl.[N:20]1([CH2:26][CH2:27][CH2:28]Cl)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.[I-].[K+]>CCOCC.C(O)C>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]([CH2:28][CH2:27][CH2:26][N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:15](=[N:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[SH:16])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7965CyclohexylamineHCID 194084-chlorobenzyl IsothiocyanateHCID 79624N-(3-chloropropyl)piperidine hydrochloride

Product 1

HCID 178528011HCID 178528011, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Cyclohexylamine (10 mmol) was added dropwise to 4-chlorobenzylisothio-cyanate (10 mmol) dissolved in 20 ml of dry ether. The solution was stirred for 2 hours at room temperature. The precipitated product was filtered off and crystallized from ethyl acetate. 3-Piperidinopropyl chloride hydrochloride (3 mmol), the product (3 mmol), and ca-talytic amounts of potassium iodide were refluxed in ethanol for 6 days. Sub-sequently, ethanol was evaporated, and the residue was purified by column chromato-graphy (eluent: methylene chloride/methanol (95/5)). After evaporation of the solvent the product was crystallized with hydrochloric acid from diethyl ether/ethanol.

Workup

  1. filtrationThe precipitated product was filtered off
  2. customcrystallized from ethyl acetate
  3. customSub-sequently, ethanol was evaporated
  4. customthe residue was purified by column chromato-graphy (eluent: methylene chloride/methanol (95/5))
  5. customAfter evaporation of the solvent the product
  6. customwas crystallized with hydrochloric acid from diethyl ether/ethanol

Sources & evidence

ORD record
ord-4d0094efd81349e6bd4a02cc191fb1ce
Source dataset
uspto-grants-2006_11
Patent number
US07138413B1

Reaction notes

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