Pyridine → HCID 21939957, compound

HRID 1242923Notes

Reaction equation

HRID 1242923 reaction equation
N1C=CC=CC=1.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=O.NC1C=C2C(=CC=1)C(=O)CCC2.[OH-].[Na+].[N+](C1C=CC([N:43]([C:47]2[CH:56]=[CH:55][C:54]3[C:53](=[O:57])[CH2:52][CH2:51][CH2:50][C:49]=3[CH:48]=2)[C:44](=[O:46])[O-])=CC=1)([O-])=O.Cl.[F:59][C:60]1[CH:65]=[CH:64][C:63]([CH:66]2[CH2:71][CH2:70][NH:69][CH2:68][CH2:67]2)=[CH:62][CH:61]=1>C(OCC)(=O)C.CS(C)=O.O1CCCC1>[F:59][C:60]1[CH:65]=[CH:64][C:63]([CH:66]2[CH2:67][CH2:68][N:69]([C:44]([NH:43][C:47]3[CH:56]=[CH:55][C:54]4[C:53](=[O:57])[CH2:52][CH2:51][CH2:50][C:49]=4[CH:48]=3)=[O:46])[CH2:70][CH2:71]2)=[CH:62][CH:61]=1

Participants

10

Reactant 6

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 821294-Nitrophenyl chloroformateHCID 3395376-Amino-1,2,3,4-tetrahydronaphthalen-1-oneHCID 218981684-(4-Fluoro-phenyl)-piperidine hydrochlorideHCID 69497326HCID 69497326, compound

Product 1

HCID 21939957HCID 21939957, compoundYield 76.5%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyridine(9.95 ml, 123 mmol) and 4-nitrophenyl chloroformate (12.4 g, 61.5 mmol) was added to a tetrahydrofuran(300 ml)solution of 6-amino-3,4-dihydro-1(2H)-naphthalenone(9.92 g, 61.5 mmol)obtained in Reference Example 96, which was stirred at room temperature for 3 hours. The solvent was distilled out under reduced pressure. 1N Hydrochloric acid was added to the residue to powder, which was washed with ethanol. 4N Aqueous sodium hydroxide solution was added to a dimethylsulfoxide (33 ml)solution of the resulting 4-nitrophenyl-5-oxo-5,6,7,8-tetrahydro-2-naphthalenylcarbamate (2.20 g, 6.74 mmol) and 4-(4-fluorophenyl)piperidine hydrochloride (1.60 g, 7.42 mmol), which was stirred at room temperature for 1 hour. Ethyl acetate was added to the reaction mixture, which was washed with 1N hydrochloric acid, aqueous potassium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was distilled out under reduced pressure. The resulting residue was purified by alumina B column chromatography (development solvent ethyl acetate), and powdered with isopropyl ether and hexane, to give the titled compound (1.89 g).

Workup

  1. customobtained in Reference Example 96, which
  2. distillationThe solvent was distilled out under reduced pressure
  3. addition1N Hydrochloric acid was added to the residue to powder, which
  4. washwas washed with ethanol
  5. stirringwas stirred at room temperature for 1 hour
  6. washwas washed with 1N hydrochloric acid, aqueous potassium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled out under reduced pressure
  9. customThe resulting residue was purified by alumina B column chromatography (development solvent ethyl acetate)

Sources & evidence

ORD record
ord-1dc6138f2be244f189d45d09848edbb3
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

Loading…