Potassium Carbonate → 4-(4-Isopropylpiperazin-1-yl)benzaldehyde

HRID 591601Notes

Reaction equation

HRID 591601 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:12])[CH3:11].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH:10]([N:13]1[CH2:18][CH2:17][N:16]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:15][CH2:14]1)([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 780131-Isopropylpiperazine

Product 1

HCID 20522144-(4-Isopropylpiperazin-1-yl)benzaldehydeYield 111.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-fluorobenzaldehyde (0.242 g, 1.95 mmol), 1-isopropylpiperazine (0.335 mL, 2.34 mmol), and K2CO3 (0.323 g, 2.34 mmol) in DMF (2.44 mL) was heated at 120° C. overnight. The mixture was diluted with EtOAc (200 mL), washed with 10% aqueous LiCl (3×75 mL) and brine (75 mL), dried over Na2SO4, and filtered. The volatiles were removed under vacuum to yield 4-(4-Isopropylpiperazin-1-yl)benzaldehyde (0.504 g) as an orange solid, which was used without further purification.

Workup

  1. washwashed with 10% aqueous LiCl (3×75 mL) and brine (75 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customThe volatiles were removed under vacuum

Sources & evidence

ORD record
ord-7a5a8143b1054655b46eda965a8fe14e
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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