Potassium Iodide → HCID 10873565, compound

HRID 722692Notes

Reaction equation

HRID 722692 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl[C:12]1[C:21]2[C:16](=[CH:17][C:18]([Cl:22])=[CH:19][CH:20]=2)[N:15]=[CH:14][CH:13]=1.[I-].[K+].Cl.[N:26]1([CH2:32][CH2:33][CH2:34]Cl)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(=O)([O-])[O-].[K+].[K+]>C1(O)C=CC=CC=1.CN(C)C=O>[Cl:22][C:18]1[CH:17]=[C:16]2[C:21]([C:12]([NH:1][CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][C:7]([O:10][CH2:34][CH2:33][CH2:32][N:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]4)=[CH:6][CH:5]=3)=[CH:13][CH:14]=[N:15]2)=[CH:20][CH:19]=1

Participants

8

Reactant 5

HCID 4875Potassium Iodide2×HCID 5610TyramineHCID 68664,7-DichloroquinolineHCID 11430Potassium CarbonateHCID 79624N-(3-chloropropyl)piperidine hydrochloride

Product 1

HCID 10873565HCID 10873565, compound

Reagents, catalysts & solvents 2

HCID 996PhenolSolventHCID 6228DimethylformamideSolvent

Procedure

Tyramine (10 mmol), 4,7-dichloroquinoline, and catalytic amounts of potassium iodide were melted in 10 g of phenol at 150° C. for 12 hours. The residue was crystallized with hydrochloric acid from ethyl acetate/water. The product (5 mmol), 3-piperidinopropylchloride hydrochloride (5 mmol), potassium carbonate (15 mmol), and catalytic amounts of potassium iodide were refluxed in N,N-dimethylformamide for 22 hours. The solvent was evaporated and the residue purified by flash chromatography (eluent: ethyl acetate/petroleum ether/triethylamine (95/50/5)). The solvent was removed under reduced pressure. The residue was crystallized with oxalic acid from diethyl ether/ethanol.

Workup

  1. customThe residue was crystallized with hydrochloric acid from ethyl acetate/water
  2. customThe solvent was evaporated
  3. customthe residue purified by flash chromatography (eluent: ethyl acetate/petroleum ether/triethylamine (95/50/5))
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was crystallized with oxalic acid from diethyl ether/ethanol

Sources & evidence

ORD record
ord-5de46443d1254e38ab08dc2641ec210a
Source dataset
uspto-grants-2006_11
Patent number
US07138413B1

Reaction notes

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