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

HRID 1644456Notes

Reaction equation

HRID 1644456 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c45d62dc8af943c4a1c2325eb6ecdc71
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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