Potassium Carbonate → HCID 22342688, compound

HRID 584246Notes

Reaction equation

HRID 584246 reaction equation
Cl.Cl.[CH2:3]1[O:18][C:17]2[CH:16]=[CH:15][C:7]([CH2:8][CH:9]3[CH2:14][NH:13][CH2:12][CH2:11][NH:10]3)=[CH:6][C:5]=2[O:4]1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:27][C:28]#[C:29][CH2:30][N:31]1[CH2:36][CH2:35][O:34][CH2:33][C:32]1([CH3:38])[CH3:37].[F:39][C:40]([F:55])([F:54])[C:41]1[CH:42]=[C:43]([CH:47]=[C:48]([C:50]([F:53])([F:52])[F:51])[CH:49]=1)[C:44](Cl)=[O:45]>CN(C)C=O>[F:39][C:40]([F:54])([F:55])[C:41]1[CH:42]=[C:43]([CH:47]=[C:48]([C:50]([F:53])([F:51])[F:52])[CH:49]=1)[C:44]([N:10]1[CH2:11][CH2:12][N:13]([CH2:27][C:28]#[C:29][CH2:30][N:31]2[CH2:36][CH2:35][O:34][CH2:33][C:32]2([CH3:38])[CH3:37])[CH2:14][CH:9]1[CH2:8][C:7]1[CH:15]=[CH:16][C:17]2[O:18][CH2:3][O:4][C:5]=2[CH:6]=1)=[O:45]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 22342632HCID 22342632, compoundHCID 22342974218594-26-4

Product 1

HCID 22342688HCID 22342688, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 2-(3,4-methylenedioxybenzyl)piperazine dihydrochloride (104 mg) and potassium carbonate (196 mg) in N,N-dimethylformamide (4 ml) was added 4-(4-chloro-2-butynyl)-3,3-dimethylmorpholine hydrochloride (84.5 mg) at 5° C. under nitrogen atmosphere and the mixture was gradually warmed to room temperature over night. To the above stirred suspension was added 3,5-bis(trifluoromethyl)benzoyl chloride (98.2 mg) at 5° C. and the mixture was stirred for 1 hour at this temperature. The mixture was extracted with ethyl acetate and the extract was washed with water, and dried over magnesium sulfate. The usual work up followed by flash chromatography on silica gel with a mixture of dichloromethane and methanol (50:1) gave 1-[3,5-bis-(trifluoromethyl)benzoyl]-4-[4-(3,3-dimethylmorpholino)-2-butynyl]-2-(3,4-methylenedioxybenzyl)piperazine, which was dissolved in ethyl acetate and treated with 4N hydrogen chloride in ethyl acetate to give 1-[3,5-bis-(trifluoromethyl)benzoyl]-4-[4-(3,3-dimethylmorpholino)-2-butynyl]-2-(3,4-methylenedioxybenzyl)piperazine dihydrochloride (107 mg) as a powder.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. additionThe usual work up followed by flash chromatography on silica gel with a mixture of dichloromethane and methanol (50:1)

Sources & evidence

ORD record
ord-e605a91bca324960936040c280855e96
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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