Potassium Iodide → HCID 66622182, compound

HRID 416231Notes

Reaction equation

HRID 416231 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][CH2:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].Cl.[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31]Cl.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[NH4+].[Cl-]>CC(C)=O>[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31][O:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][CH2:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=3)[N:10]=2)=[CH:3][C:2]=1[F:1]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 135989910HCID 135989910, compound

Product 1

HCID 66622182HCID 66622182, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 39 (450 mg, 1.27 mmol) in acetone (25 mL) was added 2-(dimethylamino)ethyl chloride hydrochloride (220 mg, 1.53 mmol) followed by potassium iodide (53 mg, 0.32 mmol) and potassium carbonate (878 mg, 6.35 mmol). The reaction mixture was refluxed for 20 h, then saturated solution of NH4Cl was added, pH of the mixture was adjusted to 8 and acetone was removed under reduced pressure. The formed solid was collected by filtration, washed with water, dried and purified by flash chromatography on silica gel (MeOH/DCM/NH4OH: 10/89/1) to afford the title compound 40 (525 mg, 1.24 mmol, 97% yield).

Workup

  1. temperatureThe reaction mixture was refluxed for 20 h
  2. customwas removed under reduced pressure
  3. filtrationThe formed solid was collected by filtration
  4. washwashed with water
  5. customdried
  6. custompurified by flash chromatography on silica gel (MeOH/DCM/NH4OH: 10/89/1)

Sources & evidence

ORD record
ord-89df743d87c2491d8a16a3c94bc7d832
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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