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

HRID 1644456ノート

反応式

HRID 1644456 の反応式
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][C:17]2=[O:26])[CH2:10][CH2:9]1)(C)(C)C.Cl.O.Cl.O1CCOCC1>O1CCOCC1>[NH2:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][C:17]2=[O:26])[CH2:10][CH2:9]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 204431481,4-Dioxane hydrochlorideHCID 86642648tert-butyl{1-[2-(2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c45d62dc8af943c4a1c2325eb6ecdc71
出典データセット
uspto-grants-2012_02
特許番号
US08124602B2

反応ノート

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