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

HRID 1006236
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HRID 1006236 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 178418397
HCID 178418397, 화합물
촉매

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온도
80 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-02ca2cf3049d4966a43346bf430d9afb
출처 데이터셋
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06787653B2

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