Chloroform → 7-[(4-aminopiperidin-1-yl)methyl]-3,4-dihydroquinolin-2(1H)-one

HRID 1256267Notes

Reaction equation

HRID 1256267 reaction equation
CCOC(C)=O.[O:7]=[C:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([NH:25]C(=O)OC(C)(C)C)[CH2:21][CH2:20]3)=[CH:13][CH:14]=2)[NH:9]1.Cl.CCOC(C)=O.C(Cl)(Cl)Cl>O>[NH2:25][CH:22]1[CH2:23][CH2:24][N:19]([CH2:18][C:12]2[CH:11]=[C:10]3[C:15]([CH2:16][CH2:17][C:8](=[O:7])[NH:9]3)=[CH:14][CH:13]=2)[CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8857Ethyl AcetateHCID 21866389Hydrogen chloride-ethyl acetateHCID 86655981Tert-butyl {1-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)methyl]piperidin-4-yl}carbamate

Product 1

HCID 673214667-[(4-aminopiperidin-1-yl)methyl]-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an EtOAc (130 mL) solution of the compound (37.8 g) obtained in Step 1-5, 4 M HCl/EtOAc solution (263 mL) was added under ice cooling and the mixture was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure. The residue was suspended in EtOAc (200 mL) and filtrated to obtain a solid. To the solid, CHCl3 (200 mL) and H2O (200 mL) were added and the mixture was stirred for 15 minutes. After a water layer and an organic layer were separated, the water layer was washed with CHCl3 twice. To the water layer, a 2 M aqueous NaOH solution was added to adjust to pH 10 and thereafter the solution was extracted 30 times with CHCl3. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (Chromatorex NH, mobile phase: MeOH/CHCl3=1/4; v/v) to obtain 7-[(4-aminopiperidin-1-yl)methyl]-3,4-dihydroquinolin-2(1H)-one (17.9 g, a colorless solid).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. filtrationfiltrated
  3. customto obtain a solid
  4. stirringthe mixture was stirred for 15 minutes
  5. customAfter a water layer and an organic layer were separated
  6. washthe water layer was washed with CHCl3 twice
  7. additionTo the water layer, a 2 M aqueous NaOH solution was added
  8. extractionthe solution was extracted 30 times with CHCl3
  9. dry with materialThe combined organic layers were dried over Na2SO4
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by column chromatography (Chromatorex NH, mobile phase: MeOH/CHCl3=1/4; v/v)

Sources & evidence

ORD record
ord-b9ad6fcc0e9e4744a6c3bb549ec13fae
Source dataset
uspto-grants-2013_06
Patent number
US08461182B2

Reaction notes

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