Potassium Hydroxide → HCID 68000203, compound

HRID 336557Notes

Reaction equation

HRID 336557 reaction equation
[OH-].[K+].C(OC(=O)[NH:7][CH:8]1[CH2:11][C:10]2([CH2:16][CH2:15][N:14]([C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[C:22]([Cl:27])[CH:23]=4)[N:18]=3)[CH2:13][CH2:12]2)[CH2:9]1)C>C(O)C.O>[Cl:27][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([N:14]1[CH2:15][CH2:16][C:10]3([CH2:9][CH:8]([NH2:7])[CH2:11]3)[CH2:12][CH2:13]1)[CH:26]=[CH:25]2

Participants

4

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 131732013HCID 131732013, compound

Product 1

HCID 68000203HCID 68000203, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
110 °C

Procedure

0.726 g (12.95 mmol) of potassium hydroxide is added, at room temperature, to a solution of 0.242 g (0.65 mmol) of ethyl[7-(6-chloroquinolin-2-yl)-7-azaspiro[3.5]non-2-yl]carbamate, obtained in step 12.5., in 3.25 mL of ethanol/water (1/1). The mixture is then heated at 110° C. for 12 hours. 0.363 g (6.47 mmol) of potassium hydroxide is added and the mixture is left stirring for 3 hours. The resulting mixture is allowed to cool to room temperature and is then concentrated under reduced pressure. The residue is taken up in dichloromethane and 1N hydrochloric acid solution. The acidic aqueous phase is washed with dichloromethane and then basified with aqueous 1N sodium hydroxide solution, which is extracted several times with dichloromethane. The combined organic phases are then dried over sodium sulfate and the filtrate is concentrated under reduced pressure. 0.188 g of expected product is thus obtained in the form of an oil.

Workup

  1. customobtained in step 12.5
  2. waitthe mixture is left
  3. temperatureto cool to room temperature
  4. concentrationis then concentrated under reduced pressure
  5. washThe acidic aqueous phase is washed with dichloromethane
  6. extractionis extracted several times with dichloromethane
  7. dry with materialThe combined organic phases are then dried over sodium sulfate
  8. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-db79ea0384814cb6a7396df9dd53d99d
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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