Hydrochloric Acid → 1-[2-(4-Aminopiperidin-1-yl)ethyl]quinolin-2(1H)-one

HRID 255329노트

반응식

HRID 255329 반응식
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([NH:20]C(=O)OC(C)(C)C)[CH2:16][CH2:15]1.Cl.O.Cl.O1CCOCC1>O1CCOCC1>[NH2:20][CH:17]1[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:10]=[CH:11][C:2]2=[O:1])[CH2:15][CH2:16]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 204431481,4-Dioxane hydrochlorideHCID 86642648tert-butyl{1-[2-(2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate2회

생성물 1

HCID 667749211-[2-(4-Aminopiperidin-1-yl)ethyl]quinolin-2(1H)-one

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

To a solution of tert-butyl {1-[2-(2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate (Intermediate 164, 220 mg, 0.59 mmol) in dioxane (5 mL) was added a solution of HCl in dioxane (4M, 9 mL), followed by water (1 mL) and it was stirred at room temperature over night. An addition 5 mL of HCl/dioxane was added to the reaction. After 1 hr, the reaction was concentrated to dryness. The crude product was partitioned between 10% methanol/dichloromethane (50 mL) and 1M sodium hydroxide (50 mL). The aqueous phase was back extracted with 10% methanol/dichloromethane (50 mL) and the combined organic phases were washed with brine, dried over sodium sulfate and concentrated under reduced pressure to give 170 mg (quantitative) of the crude product as an oil.

후처리

  1. additionwas added to the reaction
  2. concentrationthe reaction was concentrated to dryness
  3. customThe crude product was partitioned between 10% methanol/dichloromethane (50 mL) and 1M sodium hydroxide (50 mL)
  4. extractionThe aqueous phase was back extracted with 10% methanol/dichloromethane (50 mL)
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-593e5e8716664c6194401a555409720f
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875715B2

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