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

HRID 1635096Notes

Reaction equation

HRID 1635096 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:9]=[CH:10][N:11]3[C:16]([C:17]=2[O:18][CH3:19])=[C:15]([CH2:20][CH3:21])[CH:14]=[C:13]([C:22]([O:24]CC)=[O:23])[C:12]3=[O:27])[CH2:3]1.[OH-].[Li+].C(O)(=O)C>O.C1COCC1>[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:9]=[CH:10][N:11]3[C:16]([C:17]=2[O:18][CH3:19])=[C:15]([CH2:20][CH3:21])[CH:14]=[C:13]([C:22]([OH:24])=[O:23])[C:12]3=[O:27])[CH2:3]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 865895428-(3-Aminopiperidinyl)-1-Ethyl-9-Methoxy-4-Oxo-4H-Quinolizine-3-Carboxylic Acid, Ethyl Ester

Product 1

HCID 186758698-(3-Aminopiperidinyl)-1-Ethyl-9-Methoxy-4-Oxo-4H-Quinolizine-3-Carboxylic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

8-(3-aminopiperidinyl)-1-ethyl-9-methoxy-4-oxo-4H-quinolizine-3-carboxylic acid, ethyl ester (0.028 g) is dissolved in 9 ml of a 2/1 mixture of water and THF and lithium hydroxide (0.035 g) is added. The resulting solution is stirred at 60° C. for 4 days and the solution adjusted to pH 7.2 by addition of acetic acid. The title compound is collected by filtration of the precipitate.

Workup

  1. additionis added
  2. filtrationThe title compound is collected by filtration of the precipitate

Sources & evidence

ORD record
ord-60347c174eb545f8afd1c725a5fbb70e
Source dataset
uspto-grants-2003_01
Patent number
US06509349B1

Reaction notes

Loading…