1-(piperidin-1-yl)butane-1,3-dione → HCID 44627280, compound

HRID 1184025Notes

Reaction equation

HRID 1184025 reaction equation
[N:1]1([C:7](=[O:12])[CH2:8][C:9](=O)[CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26]C=1)=O.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>C(O)C>[Cl:20][C:17]1[CH:16]=[C:15]2[C:14](=[CH:19][CH:18]=1)[N:13]=[C:9]([CH3:10])[C:8]([C:7]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:12])=[C:21]2[C:22]1[CH:24]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 2467741-(piperidin-1-yl)butane-1,3-dioneHCID 2733225Ytterbium triflateHCID 68594717HCID 68594717, compound

Product 1

HCID 44627280HCID 44627280, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(piperidin-1-yl)butane-1,3-dione (1.08 g, 6.5 mmol) in ethanol (20 ml) at room temperature was added 2-amino-5-chlorophenylacetophenone (1.16 g 5.0 mmol) followed by ytterbium triflate (294 mg, 0.5 mmol). The reaction mixture was stirred at room temperature for 12 hours. The white powdery precipitate that was formed in the reaction mixture was filtered off, washed with ethanol, and dried under reduced pressure to provide (6-chloro-2-methyl-4-phenylquinolin-3-yl)(piperidin-1-yl)methanone (874 mg, 48%) as a white powder. 1H NMR (CDCl3, 400 MHz) δ 8.1 (d, 1H, J=8.6 Hz); 7.67 (dd, 1H, J=8.6, 2.3 Hz); 7.63 (d, 1H, J=2.3 Hz); 7.6-7.5 (m, 4H); 7.33-7.28 (m, 1H); 3.55 (ddd, 1H, J=13.3, 7.4, 3.1 Hz); 3.37 (ddd, 1H, J=13.3, 7.4, 3.1 Hz); 3.05 (ddd, 1H, J=13.3, 7.4, 3.1 Hz); 2.80 (ddd, 1H, J=13.3, 7.4, 3.1 Hz); 2.77 (s, 3H); 1.60-1.2 (m, 5H); 1.0 (m, 1H). LC MS (CI) shows M+H 365.

Workup

  1. customThe white powdery precipitate that was formed in the reaction mixture
  2. filtrationwas filtered off
  3. washwashed with ethanol
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-802159da904e442e873f56258e2166c2
Source dataset
uspto-grants-2014_03
Patent number
US08664399B2

Reaction notes

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