Cesium carbonate → HCID 58441936, compound

HRID 552119Notes

Reaction equation

HRID 552119 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[O:22]1[CH2:23][CH2:24][N:19]([CH2:18][CH2:17][O:1][C:2]2[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[CH:6][CH:7]=2)[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 767274-(2-Chloroethyl)morpholineHCID 2756771N-Boc-4-hydroxyaniline

Product 1

HCID 58441936HCID 58441936, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 0.1 g (0.48 mmol, 1.0 eq.) of tert-butyl 4-hydroxyphenylcarbamate in 5 mL of p-dioxane was added 0.13 g (0.72 mmol, 1.5 eq.) of 4-(2-chloroethyl)morpholine and 0.47 g (1.43 mmol, 3.0 eq.) cesium carbonate. The suspension was heated at 90° C. for 16 h. The reaction mixture was allowed to cool to room temperature and filtered. The solvent was removed in vacuo to provide tert-butyl 4-(2-morpholinoethoxy)phenylcarbamate (I-19), which was redissolved in 30% v/v TFA/methylene chloride and the resulting mixture was stirred at room temperature for 1 h. The solvent was removed in vacuo, and the residue was redissolved in methylene chloride. The organic solution was washed with sat. NaHCO3, dried (Na2SO4) and the solvent was removed in vacuo to provide 95 mg (0.43 mmol, 95%) of (4-(2-morpholinoethoxy)-benzenamine (I-20).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cb604e27944f4b4b965677f1e3d63271
Source dataset
uspto-grants-2011_05
Patent number
US07951803B2

Reaction notes

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