Toluene → 2-Methyl-1-[4-piperazinophenyl]-2-morpholino propan-1-one

HRID 1188295노트

반응식

HRID 1188295 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[C:9]([CH3:17])([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH3:10])=[CH:4][CH:3]=1.[NH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C1(C)C=CC=CC=1.C1COCC1>C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(P(C(C)(C)C)C1C(C2C=CC=CC=2)=CC=CC=1)(C)C.CC(C)([O-])C.[K+]>[CH3:10][C:9]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)([CH3:17])[C:8]([C:5]1[CH:6]=[CH:7][C:2]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:3][CH:4]=1)=[O:18]

참가 물질

9

반응물 4

HCID 1140TolueneHCID 4837PiperazineHCID 8028TetrahydrofuranHCID 157024081-(4-Chlorophenyl)-2-methyl-2-(morpholin-4-yl)propan-1-one

생성물 1

HCID 579346002-Methyl-1-[4-piperazinophenyl]-2-morpholino propan-1-one수율 96.5%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 27342152-(Di-tert-butylphosphino)biphenyl촉매HCID 23665647Potassium tert-butoxide촉매HCID 3283Diethyl Ether용매

실험 절차

Further, in a 300 mL four-neck flask provided with a stirrer, a condenser, a thermocouple, and a nitrogen inlet tube, 16 g of 1-(4-chlorophenyl)-2-methyl-2-morpholino-propan-1-one, 20.7 g of piperazine, 140 mg of palladium acetate, 360 mg of (2-biphenyl)di-tert-butylphosphine, 100 mL of toluene, 40 mL of THF, and 9.4 mg of potassium-tert-butoxide were added, followed by reaction at room temperature for 46 hours under a nitrogen stream. The reaction product was diluted with 100 mL of diethyl ether and washed with 100 mL of water, and then an organic layer was dried with anhydrous sodium sulfate. The organic layer was concentrated and then recrystallized with dichloromethane/hexane to produce 18.3 g of 2-methyl-2-morpholin-4-yl-1-(4-piperazinylphenyl)propan-1-one (10). 1H-NMR (CDCl3): 1.34 ppm (s, 6H, —CH3), 2.60 ppm (m, 4H, —CH2—), 3.05 ppm (m, 4H, —CH2—), 3.34 ppm (m, 4H, —CH2—), 3.72 ppm (m, 4H, —CH2), 6.86 ppm (m, 2H, aromatic), 8.58 ppm (m, 2H, aromatic)

후처리

  1. customFurther, in a 300 mL four-neck flask provided with a stirrer, a condenser
  2. customfollowed by reaction at room temperature for 46 hours under a nitrogen stream
  3. washwashed with 100 mL of water
  4. dry with materialan organic layer was dried with anhydrous sodium sulfate
  5. concentrationThe organic layer was concentrated
  6. customrecrystallized with dichloromethane/hexane

출처 및 근거

ORD 기록
ord-f9aa6a8aee404ccc931e30c8ff98d4db
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674089B2

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