1,4-Dioxane hydrochloride → 1-[2-(4-Aminopiperidin-1-yl)ethyl]quinolin-4(1H)-one

HRID 1644458Notes

Reaction equation

HRID 1644458 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)[C:19](=[O:26])[CH:18]=[CH:17]2)[CH2:10][CH2:9]1)(C)(C)C.Cl.O1CCOCC1.NC1CCN(CCN2C3C(=CC=CC=3)C=CC2=O)CC1>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)[C:19](=[O:26])[CH:18]=[CH:17]2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 204431481,4-Dioxane hydrochlorideHCID 667749211-[2-(4-Aminopiperidin-1-yl)ethyl]quinolin-2(1H)-oneHCID 86642649tert-Butyl{1-[2-(4-oxoquinolin-1(4H)-yl)ethyl]piperidin-4-yl}carbamate2×

Product 1

HCID 667746711-[2-(4-Aminopiperidin-1-yl)ethyl]quinolin-4(1H)-oneYield 51.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl{1-[2-(4-oxoquinolin-1(4H)-yl)ethyl]piperidin-4-yl}carbamate (Intermediate 166, 480 mg crude, 1.29 mmol) was reacted with 4M HCl/dioxane in dioxane as described for Intermediate 163 to give 180 mg (51%) of the crude product as an oil.

Sources & evidence

ORD record
ord-aac2a76e03ad410789c54f4dda6fdd3c
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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