Potassium Iodide → HCID 18982833, compound

HRID 1464604Notes

Reaction equation

HRID 1464604 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)=[O:4].[OH:15][C:16]1([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH2:22]([C:16]1([OH:15])[CH2:21][CH2:20][N:19]([CH2:2][C:3]([C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH2:8]3)=[O:4])[CH2:18][CH2:17]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 981524-Benzyl-4-piperidinolHCID 20605765-(Chloroacetyl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 18982833HCID 18982833, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-(chloroacetyl)-2(1H,3H)-indolone (2.05 g, 9.78 mmol), 4-hydroxy-4-benzylpiperidine (1.87 g, 9.78 mmol), potassium carbonate (2.97 g, 21.49 mmol), and potassium iodide (0.08 g, 0.48 mmol) in acetonitrile (200 ml) was refluxed overnight. The reaction was cooled and filtered through a celite pad. The filtrate was concentrated to give an orange foam which was flash chromatographed on silica gel with ethyl acetate elution. This afforded 0.79 g of oily yellow solid product. NMR 9.41 (br s, 1H), 7.91 (d, J=8 Hz, 1H), 7.86 (s, 1H), 7.28-7.14 (m, 5H), 6.90 d, J=8 Hz, 1H), 3.76 (s, 2H), 3.52 (s, 2H), 2.78-2.73 (m, 4H), 2.43 {t, J=10.5 Hz, 2H}, 1.86-1.76 (m, 2H), 1.50 (br d, J=12 Hz, 2H), 1.36 (br s, 1H). IR(KBr) 2920, 2815, 1710, 1685, 1615, 1240, 1115. FAB HRMS calcd for C22H25N2O3 (MH+): 365.1867. Observed m/e: 365.1883.

Workup

  1. temperaturewas refluxed overnight
  2. temperatureThe reaction was cooled
  3. filtrationfiltered through a celite pad
  4. concentrationThe filtrate was concentrated
  5. customto give an orange foam which
  6. customchromatographed on silica gel with ethyl acetate elution

Sources & evidence

ORD record
ord-f0f0abb83361455e9797f326237c33b9
Source dataset
uspto-grants-1994_04
Patent number
US05306723

Reaction notes

Loading…