Potassium Iodide → HCID 69677718, compound

HRID 584182Notes

Reaction equation

HRID 584182 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([Cl:26])[CH:25]=1)[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=1)=[O:7].Br[CH2:28][CH2:29][CH2:30][OH:31].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[Cl:2][C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([Cl:26])[CH:25]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:28][CH2:29][CH2:30][OH:31])[CH2:10][C@H:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=1)=[O:7]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 69677716HCID 69677716, compound

Product 1

HCID 69677718HCID 69677718, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (2R)-1-(3,5-dichlorobenzoyl)-2-(3,4-dimethylbenzyl)piperazine hydrochloride (300 mg), 3-bromo-1-propanol (121 mg), potassium carbonate (251 mg) and potassium iodide (24 mg) in dried acetonitrile (3 ml) was stirred at 50° C. for 10 hours. After being cooled to room temperature, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate as eluent to give (2R)-1-(3,5-dichlorobenzoyl)-2-(3,4-dimethylbenzyl)-4-(3-hydroxypropyl)piperazine as a syrup. Methanesulfonyl chloride (58 mg) was added to an ice-cooled solution of the alcohol obtained at above procedure (210 mg) and triethylamine (97.6 mg) in dichloromethane (4 ml) over 1.5 hours. After being stirred for 1 hour, the reaction mixture was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and evaporated under reduced pressure to give the corresponding mesylate. A mixture of the mesylate obtained by the above procedure, 4-aminomorpholine (59.1 mg) and triethylamine (73.2 mg) in methanol (4 ml) was stirred under reflux for 4 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel using ethyl acetate as eluent and treated with 4N hydrogen chloride in ethyl acetate solution to give (2R)-1-(3,5-dichlorobenzoyl)-2-(3,4-dimethylbenzyl)-4-(N-morpholino-3-aminopropyl)piperazine dihydrochloride.

Workup

  1. temperatureAfter being cooled to room temperature
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f6c95f4b29d1422595e89ead0909f4cf
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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