Sodium Iodide → {2-[2-(4-Octyloxy-phenyl)-morpholin-4-yl]-propyl}-phosphonic acid diethyl ester

HRID 920594Notes

Reaction equation

HRID 920594 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[O:21][CH2:20][CH2:19][NH:18][CH2:17]2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Br[CH2:23][CH2:24][CH2:25][P:26](=[O:33])([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29].[Na+].[I-].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:31]([O:30][P:26]([CH2:25][CH:24]([N:18]1[CH2:19][CH2:20][O:21][CH:16]([C:13]2[CH:12]=[CH:11][C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:15][CH:14]=2)[CH2:17]1)[CH3:23])(=[O:33])[O:27][CH2:28][CH3:29])[CH3:32]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 283500Diethyl (3-bromopropyl)phosphonateHCID 670323512-(4-Octyloxy-phenyl)-morpholine

Product 1

HCID 86670017{2-[2-(4-Octyloxy-phenyl)-morpholin-4-yl]-propyl}-phosphonic acid diethyl esterYield 66.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(4-octyloxy-phenyl)-morpholine (1.04 g; 3.6 mmol), diethyl (3-bromopropyl)phosphonate (0.82 mL; 4.3 mmol), NaI (0.11 g; 0.7 mmol), and K2CO3 (0.99 g; 7.1 mmol) in CH3CN (10 mL) was heated under reflux for 2 hours. After cooling to RT the mixture was partitioned between 5% aqueous NaHCO3 solution and Et2O. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, EtOAc: MeOH 90:10) to afford {2-[2-(4-octyloxy-phenyl)morpholin-4-yl]-propyl}-phosphonic acid diethyl ester (1.13 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customwas partitioned between 5% aqueous NaHCO3 solution and Et2O
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (SiO2, EtOAc: MeOH 90:10)

Sources & evidence

ORD record
ord-2fbb7cb398454884bb5779c2592fdf8f
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

Loading…