HCID 21278906, compound → 1-[4-(4-Amino-3-methylphenyl)piperazin-1-yl]ethan-1-one

HRID 2291565Notes

Reaction equation

HRID 2291565 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([CH3:19])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>[Pd].C(O)C>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([CH3:19])[CH:11]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 21278906HCID 21278906, compound

Product 1

HCID 212789121-[4-(4-Amino-3-methylphenyl)piperazin-1-yl]ethan-1-oneYield 94.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-Acetyl-4-(3-methyl-4-nitrophenyl)piperazine (0.5 g) and 5% palladium on carbon (0.1 g) in ethanol (20 ml) were hydrogenated at 60° and 60 p.s.i for 2 hours after which the catalyst was filtered off and the filtrate evaporated. The residue was partitioned between dichloromethane and water, and the aqueous layer extracted two more times with dichloromethane. The combined organic layers yielded 0.42 g of residue (of the title compound) on evaporation. This was recrystallized, m.p. 126°-9° (methanol/ethyl acetate).

Workup

  1. customwere hydrogenated at 60°
  2. filtration60 p.s.i for 2 hours after which the catalyst was filtered off
  3. customthe filtrate evaporated
  4. customThe residue was partitioned between dichloromethane and water
  5. extractionthe aqueous layer extracted two more times with dichloromethane

Sources & evidence

ORD record
ord-599eea5636c5419c9299f8060f3b3976
Source dataset
uspto-grants-1989_01
Patent number
US04797401

Reaction notes

Loading…