4-Methylpiperidine → HCID 25128215, compound

HRID 249669Notes

Reaction equation

HRID 249669 reaction equation
[C:1]1([N:7]2[C:19](=[O:20])[C:10]3=[CH:11][NH:12][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[C:9]3=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)C(C)C)(C)C.ClC(Cl)(O[C:34](=[O:40])OC(Cl)(Cl)Cl)Cl.[CH3:42][CH:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1>C(Cl)Cl>[CH3:42][CH:43]1[CH2:48][CH2:47][N:46]([C:34]([N:12]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:9]3=[N:8][N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:19](=[O:20])[C:10]3=[CH:11]2)=[O:40])[CH2:45][CH2:44]1

Participants

6

Reactant 4

HCID 693814-MethylpiperidineHCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 178515184HCID 178515184, compound

Product 1

HCID 25128215HCID 25128215, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-phenyl-2,5-dihydro-pyrazolo-(4,3-C)quinolin-3-one (4a) (0.261 g, 1 mM) in 2 mL of anhydrous methylene chloride was stirred with N,N-diisopropylethylamine (0.145 g, 1.2 mM) and triphosgene (0.173 g, 0.55 mM) at 0° C. for 1 hour and 25° C. for 2 hours. N,N-diisopropylethylamine (0.145 g, 1.2 mM) and 4-methylpiperidine (0.208 g, 2 mM) were added at 0° C. and the reaction mixture was stirred overnight at room temperature. The reaction was quenched by addition of aqueous sodium bicarbonate solution. The organic layer was collected, washed with brine solution, dried over sodium sulfate, filtered and concentrated in vacuo. The product was obtained by column chromatography. 1H NMR (CDCl3) δ (ppm): 1.0 (3H, d, J=6.59), 1.6 (4H, m), 1.84 (1H, m), 3.14 (1H, m), 3.30 (1H, m), 4.01, (1H, m), 4.60 (1H, m), 7.20 (1H, t, J=8.57), 7.38 (1H, m), 7.68-7.42 (4H, m), 8.18 (2H, m), 8.28 (1H, s), 8.44 (1H, d, J=8.81 Hz). m/z 387.5 (MH+).

Workup

  1. customThe reaction was quenched by addition of aqueous sodium bicarbonate solution
  2. customThe organic layer was collected
  3. washwashed with brine solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was obtained by column chromatography

Sources & evidence

ORD record
ord-9c8a46a110e3453ba08d7aee2ec3793e
Source dataset
uspto-grants-2011_01
Patent number
US07863266B2

Reaction notes

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