Piperidine → HCID 69928964, compound

HRID 1884322Notes

Reaction equation

HRID 1884322 reaction equation
C1C2C(COC([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25](=[O:48])[CH2:26][C:27]([C:30]3[C:35](=[O:36])[C:34]([CH3:37])=[C:33]([CH2:38][CH2:39][C:40]([O:42][CH2:43][CH:44]=[CH2:45])=[O:41])[C:32](=[O:46])[C:31]=3[CH3:47])([CH3:29])[CH3:28])=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CN(C=O)C>[NH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25](=[O:48])[CH2:26][C:27]([C:30]1[C:35](=[O:36])[C:34]([CH3:37])=[C:33]([CH2:38][CH2:39][C:40]([O:42][CH2:43][CH:44]=[CH2:45])=[O:41])[C:32](=[O:46])[C:31]=1[CH3:47])([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 69929129HCID 69929129, compound

Product 1

HCID 69928964HCID 69928964, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound J (250 mg, 0.38 mmol) dissolved in 10 mL of DMF was added piperidine (0.5 mL). The solution was stirred 10 min at room temperature. The solvent was evaporated and the residue was purified by flash chromatography using a gradient solvent system 10% MeOH/CH2Cl2 to 100% MeOH. After evaporation of the solvent 53 mg (33%) of the compound K was isolated as a yellow oil. 1H NMR 500 MHz (CD3OD) δ5.87 (m, 1H), 5.22 (m, 2H), 4.54 (dt, J=5.6 Hz, 1.2 Hz, 2H), 3.93 (t, J=7 Hz, 2H), 2.92 (s, 2H), 2.72 (t, J=8 Hz, 2H), 2.68 (t, J=7.5 Hz, 2H), 2.45 (t, J=8 Hz, 2H), 210 (s, 3H), 1.96 (s, 3H), 1.58-1.42 (br, 4H), 1.38 (s, 6H), 1.30 (m, 2H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography
  3. customAfter evaporation of the solvent 53 mg (33%) of the compound K
  4. customwas isolated as a yellow oil

Sources & evidence

ORD record
ord-97f8d1d9e6934178ac83541dc2c8dc76
Source dataset
uspto-grants-2004_07
Patent number
US06764768B2

Reaction notes

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