Morpholine → HCID 66579727, compound

HRID 1521820Notes

Reaction equation

HRID 1521820 reaction equation
Cl[C:2]([C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>CCOC(C)=O>[I:11][C:8]1[CH:9]=[CH:10][C:5]([C:2]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)([CH3:4])[CH3:3])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 66578779HCID 66578779, compound

Product 1

HCID 66579727HCID 66579727, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(1-Chloro-1-methylethyl)-4-iodobenzene (2 g, 7 mmol) in morpholine (10 mL) is added KI (0.5 g). The mixture is irradiated under microwave irradiation for 20 min at 160° C. (×10). The combined reaction mixtures are dissolved in EtOAc, washed with water, brine and dried over sodium sulphate. The solvent is concentrated under vacuum and purified by column chromatography (50% EtOAc in pet ether) to afford title compound as a light brown liquid. 1H NMR (DMSO-d6, 400 MHz): δ 7.65-7.63 (dd, J=2, 6.8 Hz, 2H), 7.30-7.28 (dd, J=2, 6.8 Hz, 2H), 3.53-3.65 (t, 4H), 2.33-2.31 (t, 4H), 1.22 (s, 6H).

Workup

  1. customThe mixture is irradiated under microwave irradiation for 20 min at 160° C. (×10)
  2. customThe combined reaction mixtures
  3. washwashed with water, brine
  4. dry with materialdried over sodium sulphate
  5. concentrationThe solvent is concentrated under vacuum
  6. custompurified by column chromatography (50% EtOAc in pet ether)

Sources & evidence

ORD record
ord-20fdcd3981394823b9d17f9423599a94
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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