Morpholine → HCID 53858742, compound

HRID 1108733Notes

Reaction equation

HRID 1108733 reaction equation
Cl[CH2:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:12]=2)[N:7]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[C:6]=1[CH2:26][CH2:27][CH3:28])=[O:4].[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([C:14]([O:16][CH3:17])=[O:15])[CH:9]=2)[C:5]([C:3](=[O:4])[CH2:2][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[C:6]1[CH2:26][CH2:27][CH3:28]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 22627328HCID 22627328, compound

Product 1

HCID 53858742HCID 53858742, compound

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 3-chloroacetyl-1-(2-chlorobenzyl)-2-propylindole-6-carboxylate (123 mg) and morpholine (1 ml) was stirred at 50° C. for 2.5 hours. After cooled to 20° C., the reaction mixture was extracted with ethyl acetate. The organic phase was washed with 1N hydrochloric acid and water, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:2) to give methyl 1-(2-chlorobenzyl)-3-morpholinoacetyl-2-propylindole-6-carboxylate (94 mg) as colorless amorphous.

Workup

  1. temperatureAfter cooled to 20° C.
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with 1N hydrochloric acid and water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:2)

Sources & evidence

ORD record
ord-e843214ea8eb4e8cb8151ce47777ff3f
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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