Potassium Carbonate → HCID 66653561, compound

HRID 588252Notes

Reaction equation

HRID 588252 reaction equation
[CH3:1][C:2]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[O:16][CH2:15][CH2:14][NH:13][CH2:12]2)=[CH:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+].[C:28]([O:32][C:33](=[O:38])[CH2:34][CH2:35][CH2:36]Br)([CH3:31])([CH3:30])[CH3:29]>CC#N>[C:28]([O:32][C:33](=[O:38])[CH2:34][CH2:35][CH2:36][N:13]1[CH2:14][CH2:15][O:16][CH:11]([C:8]2[CH:7]=[CH:6][C:5]([O:4][C:3]3[CH:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:2]=3[CH3:1])=[CH:10][CH:9]=2)[CH2:12]1)([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2757253tert-Butyl 4-bromobutanoateHCID 66653665HCID 66653665, compound

Product 1

HCID 66653561HCID 66653561, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-[4-(2,3-dimethyl-phenoxy)-phenyl]-morpholine (0.40 g; 1.2 mmol), K2CO3 (0.49 g; 3.6 mmol), KI (0.22 g; 1.31 mmol), 4-bromo-butyric acid tert-butyl ester (0.32 g; 1.43 mmol), and CH3CN (30 mL), was heated under reflux, overnight. After cooling to RT the mixture was concentrated in vacuo, and the residue was purified by column chromatography (SiO2, Et2O/hexanes 1:1) to afford 4-{2-[4-(2,3-dimethyl-phenoxy)-phenyl]-morpholin-4-yl}-butyric acid tert-butyl ester (0.38 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux, overnight
  3. concentrationwas concentrated in vacuo
  4. customthe residue was purified by column chromatography (SiO2, Et2O/hexanes 1:1)

Sources & evidence

ORD record
ord-ca83520bb4b649be848dd66e44ba1933
Source dataset
uspto-grants-2016_01
Patent number
US09227960B2

Reaction notes

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