Water → HCID 86713238, compound

HRID 1056829Notes

Reaction equation

HRID 1056829 reaction equation
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]1[CH:5]=[C:6]([OH:12])[C:7](=[CH:10][CH:11]=1)[CH:8]=[O:9])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.O>C(#N)C.C(OCC)(=O)C>[CH2:13]([N:3]([CH2:1][CH3:2])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[C:6]([O:12][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:5]=1)[CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 872934-(Diethylamino)-2-hydroxybenzaldehyde

Product 1

HCID 86713238HCID 86713238, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

In 90 mL of acetonitrile was dissolved 2.8 g (14.6 mmol) of 4-diethylaminosalicylaldehyde. To this solution were added 14.3 g (43.8 mmol) of cesium carbonate and 2.8 g (15.3 mmol) of 1-(2-chloroethyl)piperidine hydrochloride at room temperature and the mixture was stirred at 80° C. for 4 hours. Water (150 mL) was added to the resulting reaction mixture and extraction with ethyl acetate (100 mL×3) was performed. The combined organic layer was dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to quantitatively give 4.5 g of the title compound.

Workup

  1. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  2. filtrationAfter filtration
  3. customthe solvent was evaporated under reduced pressure to quantitatively give 4.5 g of the title compound

Sources & evidence

ORD record
ord-a90beeefb3354a45bc874b1182dfe11b
Source dataset
uspto-grants-2016_07
Patent number
US09399635B2

Reaction notes

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