Hydrochloric Acid → HCID 69677704, compound

HRID 584181Notes

Reaction equation

HRID 584181 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].Cl.[Cl:28][CH2:29][C:30]#[C:31][CH2:32][N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl>C(#N)C.C(OCC)(=O)C>[ClH:2].[ClH:28].[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]([CH2:29][C:30]#[C:31][CH2:32][N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[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

8

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 22342920HCID 22342920, compoundHCID 69677716HCID 69677716, compound

Product 1

HCID 69677704HCID 69677704, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of (2R)-1-(3,5-dichlorobenzoyl)-2-(3,4-dimethylbenzyl)piperazine hydrochloride (400 mg) and 4-(4-chloro-2-butynyl)morpholine hydrochloride (223 mg) in dried acetonitrile (4.0 ml) was stirred at 50° C. in the presence of is powdered potassium carbonate (534 mg) and potassium iodide (32 mg). After 3 hours, the reaction mixture was filtered and the insoluble material on the filter was washed with acetonitrile. The filtrate and the washing were combined and then concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and methanol (1.0:1) as eluent. The product obtained was dissolved in ethyl acetate and treated with 4N hydrogen chloride in ethyl acetate to give (2R)-1-(3,5-dichlorobenzoyl)-2-(3,4-dimethylbenzyl)-4-(4-morpholino-2-butynyl)piperazine dihydrochloride (221 mg).

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe insoluble material on the filter was washed with acetonitrile
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by column chromatography on silica gel using
  5. additiona mixture of ethyl acetate and methanol (1.0:1) as eluent
  6. customThe product obtained

Sources & evidence

ORD record
ord-ceaf01ea1935495f866362be81f2d69d
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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