1-Phenylpiperazine → HCID 10293924, compound

HRID 2086392Notes

Reaction equation

HRID 2086392 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:14]=[C:13]([CH2:15][CH2:16][CH:17]=O)[O:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:19]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:14]=[C:13]([CH2:15][CH2:16][CH2:17][N:28]3[CH2:29][CH2:30][N:25]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:26][CH2:27]3)[O:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 70961-PhenylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 22727321HCID 22727321, compound

Product 1

HCID 10293924HCID 10293924, compoundYield 56.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

About 3 min after dissolving 3-[3-(3-nitrophenyl)isoxazol-5-yl]propanal (20 mg, 0.09 mmol) and 1-phenylpiperazine (13.4, 0.09 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (56 mg, 0.26 mmol) and molecular sieves (5 beads). After the reaction was carried out for about 22 hr, the reaction mixture was diluted with ethyl acetate and washed with saturated NaHCO3 solution saturated sodium chloride solution. After drying the organic layer over anhydrous MgSO4, the solvent was removed under reduced pressure. After dissolving the residue with 1 mL of diethyl ether, HCl ether solution was slowly dropped to precipitate a white hydrochloric acid salt which was collected by filtration or centrifugation, and it was washed several times with diethyl ether. After drying the same under reduced pressure, was obtained 18.1 mg (56.8%) of the target compound.

Workup

  1. washwashed with saturated NaHCO3 solution saturated sodium chloride solution
  2. dry with materialAfter drying the organic layer over anhydrous MgSO4
  3. customthe solvent was removed under reduced pressure
  4. dissolutionAfter dissolving the residue with 1 mL of diethyl ether, HCl ether solution
  5. additionwas slowly dropped
  6. customto precipitate a white hydrochloric acid salt which
  7. filtrationwas collected by filtration or centrifugation, and it
  8. washwas washed several times with diethyl ether
  9. customAfter drying the same under reduced pressure

Sources & evidence

ORD record
ord-4bb95affcf20468d9f7c9048ccd56342
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

Loading…