Acetonitrile → 8-(3-Aminopiperidinyl)-1-Ethyl-9-Methoxy-4-Oxo-4H-Quinolizine-3-Carboxylic Acid, Ethyl Ester

HRID 1635095Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[N:14]2[C:9]([C:10]([O:18][CH3:19])=[C:11](Cl)[CH:12]=[CH:13]2)=[C:8]([CH2:20][CH3:21])[CH:7]=1)=[O:5])[CH3:2].[C:22](#[N:24])[CH3:23]>C(N(CC)CC)C>[NH2:24][CH:22]1[CH2:11][CH2:12][CH2:13][N:14]([C:11]2[CH:12]=[CH:13][N:14]3[C:9]([C:10]=2[O:18][CH3:19])=[C:8]([CH2:20][CH3:21])[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:15]3=[O:16])[CH2:23]1

Participants

Conditions

Temperature: 40 °C

Procedure

Ethyl-8-chloro-1-ethyl-9-methoxy-4-oxo-4H-quinolizine-3-carboxylate (Precursor A) (0.05 g) is dissolved in acetonitrile (3 ml) and triethylamine (0.3 ml). To this solution is added 3-S-aminopiperidine dihydrochloride (Precursor E) (0.055 g) and the mixture is stirred at 40° C. for five days. The reaction mixture is evaporated and the desired product obtained by recrystallization in isopropyl alcohol.

Workup

customThe reaction mixture is evaporated

Sources & evidence

ORD record: ord-8d075cad5dc74ba19434fcb20591b3fc
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06509349B1

Reaction notes

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