Dichloromethane → 7-methoxy-4-methyl-1-(2-(4-((3-phenylpropyl)amino)piperidin-1-yl)ethyl)quinolin-2(1H)-one

HRID 2193165Notes

Reaction equation

HRID 2193165 reaction equation
ClCCl.C(OC(=O)[N:10]([CH:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]2[C:37]3[C:32](=[CH:33][CH:34]=[C:35]([O:38][CH3:39])[CH:36]=3)[C:31]([CH3:40])=[CH:30][C:29]2=[O:41])[CH2:22][CH2:21]1)[CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>O.C(OCC)(=O)C>[CH3:39][O:38][C:35]1[CH:36]=[C:37]2[C:32]([C:31]([CH3:40])=[CH:30][C:29](=[O:41])[N:28]2[CH2:27][CH2:26][N:23]2[CH2:22][CH2:21][CH:20]([NH:10][CH2:11][CH2:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:25][CH2:24]2)=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 59398344tert-butyl (1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)(3-phenylpropyl)carbamate

Product 1

HCID 593981987-methoxy-4-methyl-1-(2-(4-((3-phenylpropyl)amino)piperidin-1-yl)ethyl)quinolin-2(1H)-oneYield 84.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 2 mL of a dichloromethane solution containing 0.16 g of tert-butyl(1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)(3-phenylpropyl)carbamate, 0.5 mL of trifluoroacetic acid was added under ice-cooling and stirred for 1.5 hours, thereafter the mixture was raised to the room temperature and left to stand for one night. The solvent was removed under reduced pressure, and to the residue thus obtained, ethyl acetate and water were added, and adjusted to pH 12.3 with 20% aqueous sodium hydroxide solution. The organic layer was separated, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 0.11 g of 7-methoxy-4-methyl-1-(2-(4-((3-phenylpropyl)amino)piperidin-1-yl)ethyl)quinolin-2(1H)-one as a yellow oil.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. waitleft
  4. waitto stand for one night
  5. customThe solvent was removed under reduced pressure
  6. customto the residue thus obtained
  7. customThe organic layer was separated
  8. washwashed with aqueous saturated sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8a262ebb4e3e4b85a067062db2ceba7e
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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