Isopropyl iodide → Methyl 2-(2-(benzyloxy)-5-(1-isopropylpiperidin-4-yl)benzamido)-4-phenylbenzoate

HRID 454722Notes

Reaction equation

HRID 454722 reaction equation
[CH:1](I)([CH3:3])[CH3:2].[CH2:5]([O:12][C:13]1[CH:37]=[CH:36][C:35]([CH:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)=[CH:34][C:14]=1[C:15]([NH:17][C:18]1[CH:27]=[C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=[CH:24][C:19]=1[C:20]([O:22][CH3:23])=[O:21])=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>C(=O)([O-])[O-].[K+].[K+].C(#N)C>[CH2:5]([O:12][C:13]1[CH:37]=[CH:36][C:35]([CH:38]2[CH2:39][CH2:40][N:41]([CH:1]([CH3:3])[CH3:2])[CH2:42][CH2:43]2)=[CH:34][C:14]=1[C:15]([NH:17][C:18]1[CH:27]=[C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=[CH:24][C:19]=1[C:20]([O:22][CH3:23])=[O:21])=[O:16])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 6362Isopropyl iodide2×HCID 11430Potassium CarbonateHCID 66990546Methyl 2-(2-(benzyloxy)-5-(piperidin-4-yl)benzamido)-4-phenylbenzoate

Product 1

HCID 66989977Methyl 2-(2-(benzyloxy)-5-(1-isopropylpiperidin-4-yl)benzamido)-4-phenylbenzoate

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateCatalystHCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (0.033 mg) and isopropyl iodide (0.024 mL) were sequentially added to an acetonitrile (1.9 mL) suspension of methyl 2-(2-(benzyloxy)-5-(piperidin-4-yl)benzamido)-4-phenylbenzoate (0.13 g), followed by heating to reflux for 1 hour. The reaction mixture was cooled to room temperature, and potassium carbonate (6.7 mg) and isopropyl iodide (4.8 μL) were sequentially added thereto, followed by heating to reflux for 2 hours. After cooling the reaction mixture to room temperature, the solvent was evaporated under reduced pressure, and ethyl acetate and a saturated aqueous solution of sodium bicarbonate were added to the residue. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-95% chloroform/methanol] to obtain 0.12 g of methyl 2-(2-(benzyloxy)-5-(1-isopropylpiperidin-4-yl)benzamido)-4-phenylbenzoate as an orange oily sub stance.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 1 hour
  3. temperatureby heating
  4. temperatureto reflux for 2 hours
  5. temperatureAfter cooling the reaction mixture to room temperature
  6. customthe solvent was evaporated under reduced pressure, and ethyl acetate
  7. additiona saturated aqueous solution of sodium bicarbonate were added to the residue
  8. customThe organic layer was separated
  9. washwashed with a saturated aqueous solution of sodium chloride
  10. dry with materialdried over anhydrous sodium sulfate
  11. customthe solvent was evaporated under reduced pressure
  12. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-95% chloroform/methanol]

Sources & evidence

ORD record
ord-b1dffccf4d49430e967614e7a35604ae
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

Loading…