Piperidine → 2-[2-[(phenylmethyl)thio]phenyl]-4(1H)-quinolinone

HRID 483355Notes

Reaction equation

HRID 483355 reaction equation
[C:1]1([CH2:7][S:8][C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[CH:11]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24](=[O:29])[CH2:25]S(C)=O.N1CCCCC1>C1(C)C=CC=CC=1>[C:1]1([CH2:7][S:8][C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]2[NH:17][C:18]3[C:19]([C:24](=[O:29])[CH:25]=2)=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 111178092-(Benzylsulfanyl)benzaldehydeHCID 143584271-(2-Aminophenyl)-2-(methylsulfinyl)ethanone

Product 1

HCID 152289892-[2-[(phenylmethyl)thio]phenyl]-4(1H)-quinolinoneYield 55.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-[(Phenylmethyl)thio]benzaldehyde (2.28 g, 10 mmole, 1 equiv.), 1-(2-aminophenyl)-2-(methylsulfinyl)ethanone (1.97 g, 10 mmole, 1 equiv.), and piperidine (0.5 ml, 5 mmole, 0.5 equiv.) were combined in toluene (50 ml), and the mixture was heated to reflux under a Dean-Stark trap. After 3 hr, the reaction was concentrated and the residue was chromatographed on silica gel (50% EtOAc/CHCl3) to afford 2-[2-[(phenylmethyl)thio]phenyl]-4(1H)-quinolinone (1.90 g, 55%) as a brownish-yellow foam. Recrystallization from CHCl3 /EtOAc gave light yellow crystals (1.39 g): mp 196-197° C.; TLC (50% EtOAc/CHCl3) Rf 0.31; 1H NMR (CDCl3) δ8.63 (br s, 1 H), 8.36 (dd, J=8.1, 0.8 Hz, 1 H), 7.50-7.62 (m, 2 H), 7.28-7.45 (m, 4 H), 7.16-7.26 (m, 4 H), 7.00-7.08 (m, 2 H), 6.24 (d, J=1.8 Hz, 1 H), 3.97 (s, 2 H); IR (KBr) 2100-3200 (br), 1632, 1594, 1530, 1497, 1439 cm-1 ; MS (NH3), m/e (%) 344.1 (100, (M+H)+), 254.2 (26.9). Anal. Calcd for C22H17NOS: C, 76.54; H, 4.87; N, 3.91; S, 9.12. Found: C, 76.94; H, 4.99; N, 4.08; S, 9.34.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux under a Dean-Stark trap
  3. concentrationthe reaction was concentrated
  4. customthe residue was chromatographed on silica gel (50% EtOAc/CHCl3)

Sources & evidence

ORD record
ord-7e75d40a27184b8499fa82fd7b9f770a
Source dataset
uspto-grants-1993_07
Patent number
US05225418

Reaction notes

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