Iodoethane → HCID 72187885, compound

HRID 515164Notes

Reaction equation

HRID 515164 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:25])[C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:13][C:12]=2[OH:24])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:32](I)[CH3:33]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:25])[C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[CH:13][C:12]=2[O:24][CH2:32][CH3:33])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6340Iodoethane3×HCID 11430Potassium CarbonateHCID 86699734HCID 86699734, compound

Product 1

HCID 72187885HCID 72187885, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-[(4-chlorophenyl)-methyl]-2-hydroxy-6-methyl-4-morpholin-4-yl-benzamide (0.2 g, 0.56 mmol) in acetone (5 ml) are added potassium carbonate (0.092 g, 0.66 mmol) and ethyl iodide (0.066 ml, 0.83 mmol). The reaction mixture is stirred at 50° C. for 1 h. Additional ethyl iodide (0.22 ml, 2.77 mmol) is added and heating is continued for another 2 h. Additional ethyl iodide (0.22 ml, 2.77 mmol) is then added and the reaction mixture is stirred for 15 h. After completion of reaction, the solution is filtered through a pad of celite and concentrated to obtain the crude product, which is purified by column chromatography (silica gel, 15% ethyl acetate/hexan) yielding N-[(4-chlorophenyl)-methyl]-2-ethoxy-6-methyl-4-morpholin-4-yl-benzamide (example 11) (0.12 g, 0.3 mmol, 56%). [M+H]+ 389.2.

Workup

  1. temperatureheating
  2. waitis continued for another 2 h
  3. stirringthe reaction mixture is stirred for 15 h
  4. customAfter completion of reaction
  5. filtrationthe solution is filtered through a pad of celite
  6. concentrationconcentrated
  7. customto obtain the crude product, which
  8. customis purified by column chromatography (silica gel, 15% ethyl acetate/hexan)

Sources & evidence

ORD record
ord-7e755d4f9ea04846bc00aa0c354651c8
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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