Triethylamine → 1-[4-[2-(4,4-Diethylcyclohexyl)phenyl]piperazin-1-yl]butan-1-one

HRID 32211

반응식

HRID 32211 반응식
[CH2:1]([C:3]1([CH2:21][CH3:22])[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH2:5][CH2:4]1)[CH3:2].C(N(CC)CC)C.[C:30](Cl)(=[O:34])[CH2:31][CH2:32][CH3:33].C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:21]([C:3]1([CH2:1][CH3:2])[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]2[CH2:16][CH2:17][N:18]([C:30](=[O:34])[CH2:31][CH2:32][CH3:33])[CH2:19][CH2:20]2)[CH2:5][CH2:4]1)[CH3:22]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 516892Sodium BicarbonateHCID 23141791HCID 23141791, 화합물

생성물 1

HCID 231423061-[4-[2-(4,4-Diethylcyclohexyl)phenyl]piperazin-1-yl]butan-1-one수율 72.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a solution of 1-[2-(4,4-diethylcyclohexyl)phenyl]piperazine (30 mg, 0.10 mmol) produced in Example (83a) in tetrahydrofuran (1 mL) was added triethylamine (15 mg, 0.15 mmol), followed by stirring at an external temperature of 0° C. Butyryl chloride (0.015 mL, 0.14 mmol) was added to the reaction mixture while stirring, and the stirring was continued for 9 hours and 30 minutes at an external temperature of 0° C. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with water and filtered through Celite, and the filtrate was concentrated. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 27 mg of the title compound as a yellow solid.

후처리

  1. stirringwhile stirring
  2. washThe organic layer was washed with water
  3. filtrationfiltered through Celite
  4. concentrationthe filtrate was concentrated
  5. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

출처 및 근거

ORD 기록
ord-3e5da6e87039406598083fca518c824f
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425554B2

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