p-Toluenesulfonic acid monohydrate → HCID 59424354, compound

HRID 501978Notes

Reaction equation

HRID 501978 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[CH:23](O)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:25])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[C:15](=[O:25])[NH:16][C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 59424399HCID 59424399, compound

Product 1

HCID 59424354HCID 59424354, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-(1-Benzylpiperidin-4-yl)-4-hydroxy-3,4-dihydroquinolin-2(1H)-one (550 mg, 1.6 mmol) was suspended in benzene (10 mL). p-Toluenesulfonic acid monohydrate (370 mg, 1.9 mmol) was added to the mixture. The reaction was heated to reflux and held there for 1 h. The reaction mixture was concentrated in vacuo. The resulting residue was dissolved in 10% ethanol/dichloromethane (50 mL) and washed with aqueous sodium bicarbonate (2×). The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was triturated with diethyl ether to give a solid which was filtered, washed with diethyl ether, and dried in vacuo. The title compound was obtained as off-white solid in 63% yield. 1H NMR (300 MHz, DMSO-d6): δ 11.72 (s, 1H), 7.72 (s, 1H), 7.62 (d, J=6.95, 1H), 7.47-7.38 (m, 1H), 7.35-7.30 (m, 4H), 7.29-7.20 (m, 2H), 7.14 (t, J=7.50, 1H), 3.49 (s, 3H), 2.92 (d, J=11.34, 2H), 2.83-2.69 (m, 1H), 2.04 (t, J=10.61, 2H), 1.78 (d, J=12.08, 2H), 1.71-1.47 (m, 2H). Mass spec.: 319.3 (MH)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionThe resulting residue was dissolved in 10% ethanol/dichloromethane (50 mL)
  5. washwashed with aqueous sodium bicarbonate (2×)
  6. dry with materialThe organic layer was dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with diethyl ether
  10. customto give a solid which
  11. filtrationwas filtered
  12. washwashed with diethyl ether
  13. customdried in vacuo

Sources & evidence

ORD record
ord-2d956752548c41f6899243d2829988f4
Source dataset
uspto-grants-2010_08
Patent number
US07772244B2

Reaction notes

Loading…