Sodium Carbonate → 1,3-Bis[4-[4-(4-isopropoxy-3,5-dimethoxyphenyl)benzoyl]-1-piperazinyl]propane

HRID 1006236Notes

Reaction equation

HRID 1006236 reaction equation
[C:1](=[O:4])([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:39]=[CH:38][C:11]([C:12]([N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][N:26]([C:29](=[O:37])[C:30]4[CH:35]=[CH:34][C:33](Br)=[CH:32][CH:31]=4)[CH2:25][CH2:24]3)[CH2:16][CH2:15]2)=[O:13])=[CH:10][CH:9]=1.[CH:40]([O:43][C:44]1[C:49]([O:50][CH3:51])=[CH:48][C:47](B(O)O)=[CH:46][C:45]=1[O:55][CH3:56])([CH3:42])[CH3:41]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:40]([O:43][C:44]1[C:45]([O:55][CH3:56])=[CH:46][C:47]([C:33]2[CH:32]=[CH:31][C:30]([C:29]([N:26]3[CH2:25][CH2:24][N:23]([CH2:22][CH2:21][CH2:20][N:17]4[CH2:18][CH2:19][N:14]([C:12](=[O:13])[C:11]5[CH:10]=[CH:9][C:8]([C:47]6[CH:48]=[C:49]([O:50][CH3:51])[C:44]([O:43][CH:40]([CH3:42])[CH3:41])=[C:45]([O:55][CH3:56])[CH:46]=6)=[CH:39][CH:38]=5)[CH2:15][CH2:16]4)[CH2:28][CH2:27]3)=[O:37])=[CH:35][CH:34]=2)=[CH:48][C:49]=1[O:4][CH3:1])([CH3:42])[CH3:41]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 116927231,3-Bis[4-(4-bromobenzoyl)-1-piperazinyl]propaneHCID 224855944-Isopropoxy-3,5-dimethoxyphenylboronic acid

Product 1

HCID 104407901,3-Bis[4-[4-(4-isopropoxy-3,5-dimethoxyphenyl)benzoyl]-1-piperazinyl]propaneYield 94%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

Under nitrogen were added 2.40 mL (48 mmol) of a 2 mol/L aqueous sodium carbonate solution and 729.9 mg (0.632 mmol) of tetrakis(triphenylphosphine)palladium (0) to a solution of 4.50 g (7.79 mmol) of 1,3-bis[4-(4-bromobenzoyl)-1-piperazinyl]propane and 4.50 g (18.7 mmol) of 4-isopropoxy-3,5-dimethoxyphenylboronic acid in ethanol-toluene (15 mL -60 mL), and the mixture was stirred for 3 hours at 80° C. The reaction mixture was concentrated under reduced pressure to remove the organic solvents. Water (15 mL) was added to the residue and the mixture was extracted with chloroform (100 mL, 3×30 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to give 5.93 g of 1,3-bis[4-[4-(4-isopropoxy-3,5-dimethoxyphenyl)benzoyl]-1-piperazinyl]propane as a colorless oil (yield 94%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove the organic solvents
  3. additionWater (15 mL) was added to the residue
  4. extractionthe mixture was extracted with chloroform (100 mL, 3×30 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-02ca2cf3049d4966a43346bf430d9afb
Source dataset
uspto-grants-2004_09
Patent number
US06787653B2

Reaction notes

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