p-Toluenesulfonic acid monohydrate → HCID 59424354, compound

HRID 1172357Notes

Reaction equation

HRID 1172357 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 (1.6 mmol, 550 mg) was suspended in benzene (10 mL). p-Toluenesulfonic acid monohydrate (1.9 mmol, 370 mg) was added to the mixture. Reaction was heated to reflux and held for 1 hour. Reaction mixture was concentrated in vacuo. Residue was dissolved in 10% ethanol-dichloromethane (50 mL). Mixture was washed 2× with aqueous sodium bicarbonate. Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Residue was triturated with diethyl ether. Solids were filtered off, washed with diethyl ether, then dried in vacuo. 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). MS m/e (M+H)+=319.3.

Workup

  1. customReaction
  2. temperaturewas heated
  3. temperatureto reflux
  4. customReaction mixture
  5. concentrationwas concentrated in vacuo
  6. dissolutionResidue was dissolved in 10% ethanol-dichloromethane (50 mL)
  7. washMixture was washed 2× with aqueous sodium bicarbonate
  8. dry with materialOrganic layer was dried (magnesium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customResidue was triturated with diethyl ether
  12. filtrationSolids were filtered off
  13. washwashed with diethyl ether
  14. customdried in vacuo

Sources & evidence

ORD record
ord-07d96790f1064a8f9f4c4ca392f357ce
Source dataset
uspto-grants-2010_11
Patent number
US07834007B2

Reaction notes

Loading…