4-Fluorobenzaldehyde → HCID 54525922, compound

HRID 1596229Notes

Reaction equation

HRID 1596229 reaction equation
Cl.Cl.[C:3]([N:6]1[CH2:11][CH2:10][N:9]([NH2:12])[CH2:8][CH2:7]1)(=[O:5])[CH3:4].[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1>C(O)C.C(N(CC)CC)C>[C:3]([N:6]1[CH2:11][CH2:10][N:9]([N:12]=[CH:18][C:17]2[CH:20]=[CH:21][C:14]([F:13])=[CH:15][CH:16]=2)[CH2:8][CH2:7]1)(=[O:5])[CH3:4]

Participants

5

Reactant 2

HCID 680234-FluorobenzaldehydeHCID 21701657HCID 21701657, compound

Product 1

HCID 54525922HCID 54525922, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-acetyl-4-aminopiperazine dihydrochloride (300 mg) in ethanol (10 ml) and triethylamine (0.78 ml) was added p-fluorobenzaldehyde (0.164 ml), and the mixture was heated at 80° C. for 2 hours. After removal of the solvent in vacuo, the residue was triturated with ethyl acetate and water. The organic layer was separated, dried over magnesium sulfate, and concentrated. The residue was crystallized from diisopropyl ether to give 1-acetyl-4-(4-fluorobenzylidene)aminopiperazine (0.15 g).

Workup

  1. customAfter removal of the solvent in vacuo
  2. customthe residue was triturated with ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-691f23435a8f4e659064e673779ee133
Source dataset
uspto-grants-2001_09
Patent number
US06291464B1

Reaction notes

Loading…