Morpholine → HCID 53858742, compound

HRID 278117Notes

Reaction equation

HRID 278117 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-morpholineacetyl-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-6f531a4fb7ee455a8fdfc34eb6e41d57
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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