1-Phenylpiperazine → HCID 86684883, compound

HRID 238385Notes

Reaction equation

HRID 238385 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC(CO[C:20]2[N:24]([CH3:25])[N:23]=[CH:22][C:21]=2[CH:26]=[O:27])=CC=1.C(N(CC)CC)C>CN(C)C=O>[CH3:25][N:24]1[C:20]([N:10]2[CH2:11][CH2:12][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH2:9]2)=[C:21]([CH:26]=[O:27])[CH:22]=[N:23]1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 86684882HCID 86684882, compound

Product 1

HCID 86684883HCID 86684883, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-phenylpiperazine (3.40 g), 5-[(4-chlorobenzyl)oxy]-1-methyl-1H-pyrazol-4-carbaldehyde (600 mg), triethylamine (1.20 mL) and dimethylformamide (7.0 mL) was stirred at 120° C. for 8 hours, and then at a room temperature for 17 hours. Thereafter, the reaction solution was concentrated under a reduced pressure, and water was then added thereto. The obtained mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline, and was then dried over anhydrous sodium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=80:20 to 10:90), so as to obtain the title compound (669 mg) in the form of a light yellow solid.

Workup

  1. waitat a room temperature for 17 hours
  2. concentrationThereafter, the reaction solution was concentrated under a reduced pressure, and water
  3. additionwas then added
  4. extractionThe obtained mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated saline, and was then dried over anhydrous sodium sulfate
  7. concentrationfollowed by vacuum concentration
  8. customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=80:20 to 10:90)

Sources & evidence

ORD record
ord-87197779fa3a49caabdcb9286e3c4e28
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

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