Water → HCID 22597936, compound

HRID 1760228Notes

Reaction equation

HRID 1760228 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[CH2:14][CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]1[C:30]([O:32]C)=[O:31])=[CH:11][C:10]([O:34][CH3:35])=[CH:9][CH:8]=2.C(OCC)C.O>O1CCOCC1>[Cl:3][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[CH2:14][CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[CH2:19][CH:18]1[C:30]([OH:32])=[O:31])=[CH:11][C:10]([O:34][CH3:35])=[CH:9][CH:8]=2

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 86591956HCID 86591956, compound

Product 1

HCID 22597936HCID 22597936, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

60 cm3 of a 1 N aqueous sodium hydroxide solution are added to 7.05 g of methyl (3RS,4RS)-4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-carboxylate in 100 cm3 of dioxane. The reaction medium is then heated at 60° C. for 2 hours and then concentrated to dryness under reduced pressure (45° C.; 5 kPa). The residue obtained is taken up with 300 cm3 of diethyl ether and 500 cm3 of distilled water. The aqueous phase is then washed with 200 cm3 of diethyl ether and then acidified with 55 cm3 of a 1 N aqueous hydrochloric acid solution. Re-extraction is then carried out with 2 times 250 cm3 of ethyl acetate. The pooled organic phases are dried over magnesium sulfate for 1 hour, then filtration is carried out through a sintered glass funnel and evaporation is carried out under reduced pressure (45° C.; 5 kPa). 5.5 g of (3RS,4RS)-4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-carboxylic acid, in the form of a white solid, are obtained.

Workup

  1. concentrationconcentrated to dryness under reduced pressure (45° C.; 5 kPa)
  2. customThe residue obtained
  3. washThe aqueous phase is then washed with 200 cm3 of diethyl ether
  4. dry with materialThe pooled organic phases are dried over magnesium sulfate for 1 hour
  5. filtrationfiltration
  6. customis carried out through a sintered glass funnel
  7. customevaporation
  8. customis carried out under reduced pressure (45° C.; 5 kPa)

Sources & evidence

ORD record
ord-2041ffc848dc4f56ae8f48fbe590cfa6
Source dataset
uspto-grants-2005_01
Patent number
US06841562B2

Reaction notes

Loading…