Potassium Carbonate → HCID 49850482, compound

HRID 403110Notes

Reaction equation

HRID 403110 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[C:25]1([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:24][O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][N:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:34]1[CH2:35][CH2:36][CH:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:32][CH2:33]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 698734-PhenylpiperidineHCID 67128562HCID 67128562, compound

Product 1

HCID 49850482HCID 49850482, compoundYield 60.75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound 2 (0.31 g, 0.8 mmol), 4-phenylpiperidine (0.2 g, 1.2 mmol) and K2CO3 (0.166 g, 1.2 mmol) were added to 50 mL CH3CN, and the solution was refluxed under argon atmosphere for 16 h. After cooling to room temperature, the solvent was evaporated to dryness. Purification was carried out on a silica gel TLC plate that was developed in 4% methanolic NH3 (7 M NH3 in methanol)/96% CH2Cl2. The product was obtained as pale yellow oil (60.75%). 1H NMR (CDCl3) δ 8.489 (dd, 1H, Ar), 7.624 (ddd, 1H, Ar), 7.572 (d, 1H, Ar), 7.497 (dd, 1H, Ar), 7.290 (t, 2H, Ar), 7.203 (m, 4H, Ar), 7.106 (m, 1H, Ar), 6.936 (ddd, 1H, Ar), 6.836 (d, 1H, Ar), 3.792 (s, 3H, —OCH3), 3.763 (s, 2H, —CH2—), 3.667 (s, 2H, —CH2—), 3.063 (m, 2H, —CH2—), 2.486 (t, 3H, —CH—CH2—), 2.336 (s(br), 2H, —CH2—), 2.041 (s(br), 2H, —CH2—), 1.836 (s(br), 4H, —CH2—CH2—), 1.543 (m, 4H, —CH2—CH2—), 1.300 (m, 2H, —CH2—), 1.238 (m, 2H, —CH2—). Mass Spect.=471.68 (M+H)+.

Workup

  1. temperaturethe solution was refluxed under argon atmosphere for 16 h
  2. customthe solvent was evaporated to dryness
  3. customPurification

Sources & evidence

ORD record
ord-bcb8e581253d4d23ad1db6be4e6304b5
Source dataset
uspto-grants-2014_06
Patent number
US08747810B2

Reaction notes

Loading…