Morpholine → HCID 85868160, compound

HRID 1925811Notes

Reaction equation

HRID 1925811 reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][O:8][CH2:9][CH2:10]Br)([CH3:4])([CH3:3])[CH3:2].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:12])[NH:7][O:8][CH2:9][CH2:10][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 85868158606143-96-8

Product 1

HCID 85868160HCID 85868160, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (2-bromo-ethoxy)-carbamic acid tert-butyl ester (252 mg, 1.05 mmol) in DMF (2 mL) at room temperature is added morpholine (0.14 mL, 1.6 mmol). The reaction mixture is stirred for 7 hours at 50° C. The reaction mixture is diluted with EtOAc, and washed with water. The organic layer is dried over MgSO4, filtered, concentrated, and purified by flash chromatography (2% MeOH in CH2Cl2) to give the desired product (118 mg, 46%): MS APCI (+) m/z 247 detected.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography (2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-f2d306ed0e394b36a3a25bba74421a53
Source dataset
uspto-grants-2012_05
Patent number
US08178693B2

Reaction notes

Loading…