Potassium Iodide → 4-[2-(4-Octyloxy-phenyl)-morpholin-4-yl]-butyric acid tert-butyl ester

HRID 2167891Notes

Reaction equation

HRID 2167891 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].[C:22]([O:26][C:27](=[O:32])[CH2:28][CH2:29][CH2:30]Br)([CH3:25])([CH3:24])[CH3:23].[I-].[K+].C([O-])([O-])=O.[K+].[K+]>CC#N>[C:22]([O:26][C:27](=[O:32])[CH2:28][CH2:29][CH2:30][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)([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2757253tert-Butyl 4-bromobutanoateHCID 670323512-(4-Octyloxy-phenyl)-morpholine

Product 1

HCID 670329804-[2-(4-Octyloxy-phenyl)-morpholin-4-yl]-butyric acid tert-butyl esterYield 84.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(4-Octyloxy-phenyl)-morpholine (1.50 g; 5.2 mmol), 4-bromo-butyric acid tert-butyl ester (1.38 g; 6.2 mmol) (prepared according to C. Morin, M. Vidal Tetrahedron, 1992, 48(42), 9277), potassium iodide (1.03 g; 6.2 mmol), K2CO3 (1.42 g; 10.29 mmol), and CH3CN (15 mL) were mixed and heated under reflux for 2 hours. After cooling to RT the reaction mixture was concentrated in vacuo, dissolved in EtOAc, washed with 5% aqueous NaHCO3 solution, dried (Na2SO4) concentrated in vacuo and purified by column chromatography (SiO2, Et2O:hexanes 1:1) to afford 4-[2-(4-octyloxy-phenyl)-morpholin-4-yl]-butyric acid tert-butyl ester (1.90 g), TLC (SiO2 Rf. 0.20 EtOAc:hexanes 1:1)

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. concentrationwas concentrated in vacuo
  4. dissolutiondissolved in EtOAc
  5. washwashed with 5% aqueous NaHCO3 solution
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. custompurified by column chromatography (SiO2, Et2O:hexanes 1:1)

Sources & evidence

ORD record
ord-fe5719989c6445f9ba1b687aed371ad9
Source dataset
uspto-grants-2015_06
Patent number
US09045441B2

Reaction notes

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