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

HRID 1188295ノート

反応式

HRID 1188295 の反応式
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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 27342152-(Di-tert-butylphosphino)biphenyl触媒HCID 23665647Potassium tert-butoxide触媒HCID 3283Diethyl Ether溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-f9aa6a8aee404ccc931e30c8ff98d4db
出典データセット
uspto-grants-2014_03
特許番号
US08674089B2

反応ノート

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