m-Anisoyl chloride → 3-methoxy-N-{1-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)methyl]piperidin-4-yl}benzamide

HRID 1256268Notes

Reaction equation

HRID 1256268 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][C:15](=[O:19])[NH:16]3)=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34](Cl)=[O:35].C([O-])(O)=O.[Na+]>CC(O)C.C(Cl)(Cl)Cl>[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34]([NH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][C:15](=[O:19])[NH:16]3)=[CH:11][CH:10]=2)[CH2:4][CH2:3]1)=[O:35]

Participants

7

Reactant 4

HCID 74374m-Anisoyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 673214667-[(4-aminopiperidin-1-yl)methyl]-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 452557883-methoxy-N-{1-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)methyl]piperidin-4-yl}benzamide

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

To a CHCl3 (5.00 mL) solution of the compound (250 mg) obtained in Step 1-6, iPr2NEt (370 μL) and 3-methoxybenzoyl chloride (180 mg) were added and the mixture was stirred at room temperature for three days. To the reaction mixture, a saturated aqueous NaHCO3 solution was added and the solution was extracted with CHCl3 four times. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography [(silica gel 60 N, mobile phase: MeOH/CHCl3=0/100 to 10/90; v/v) and (Chromatorex NH, mobile phase: CHCl3) in this order] to obtain a solid. To the solid obtained, IPA was added at room temperature and the mixture was stirred for one hour, filtrated and washed with IPA and hexane to obtain the titled compound (159 mg, a colorless solid).

Workup

  1. extractionthe solution was extracted with CHCl3 four times
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography [(silica gel 60 N, mobile phase: MeOH/CHCl3=0/100 to 10/90; v/v) and (Chromatorex NH, mobile phase: CHCl3) in this order]
  5. customto obtain a solid
  6. customTo the solid obtained
  7. stirringthe mixture was stirred for one hour
  8. filtrationfiltrated
  9. washwashed with IPA and hexane

Sources & evidence

ORD record
ord-17f7d7e6e10547d3bfb3eb5da99aa776
Source dataset
uspto-grants-2013_06
Patent number
US08461182B2

Reaction notes

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