1-Phenylpiperazine → HCID 22762587, compound

HRID 1112738Notes

Reaction equation

HRID 1112738 reaction equation
[CH2:1]([NH:10][C:11](=[O:15])[CH2:12][CH2:13]Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[C:16]1([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[CH2:1]([NH:10][C:11](=[O:15])[CH2:12][CH2:13][N:25]1[CH2:26][CH2:27][N:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:23][CH2:24]1)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 10340Sodium CarbonateHCID 22762545HCID 22762545, compound

Product 1

HCID 22762587HCID 22762587, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of N-phenacyl-3-bromopropanamide (10.2 g; 0.038 mole) and N-phenylpiperazine (12.0 g; 0.074 mole) in dry DMF (100 ml) was stirred with anhydrous, finely-powdered sodium carbonate (15.0 g) for 18 hours at room temperature. The temperature was then increased to 80° C. and held for 12 hours to complete the reaction. The DMF was evaporated off under vacuum and the residue diluted with water (100 ml). The mixture was extracted with chloroform (3 × 100 ml). The extracts were shaken with 2 × 100 ml 2N HCl and the organic layer discarded. The aqueous layer was basified with NaOH solution to pH 9 and extracted with 3 × 75 ml CHCl3. The extracts were washed with water and dried. After removal of the solvent the remaining viscous gum triturated with ether to give a buff-coloured solid. After recrystallisation from isopropanol the product weighed 6.0 g and melted at 126° C.

Workup

  1. customthe reaction
  2. customThe DMF was evaporated off under vacuum
  3. additionthe residue diluted with water (100 ml)
  4. extractionThe mixture was extracted with chloroform (3 × 100 ml)
  5. extractionextracted with 3 × 75 ml CHCl3
  6. washThe extracts were washed with water
  7. customdried
  8. customAfter removal of the solvent the remaining viscous gum
  9. customtriturated with ether
  10. customto give a buff-coloured solid
  11. customAfter recrystallisation from isopropanol the product

Sources & evidence

ORD record
ord-ab5c6fe7e50e4cf4bedafb686dac64ff
Source dataset
uspto-grants-1978_10
Patent number
US04123529

Reaction notes

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