Water → (1H-Indol-6-yl)(morpholino)methanone

HRID 630439Notes

Reaction equation

HRID 630439 reaction equation
ON1C2N=CC=CC=2N=N1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26](O)=[O:27])[CH:24]=2)[CH:19]=[CH:18]1.O>CN(C=O)C>[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[O:27])[CH:24]=2)[CH:19]=[CH:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 181649HOAtHCID 5952301H-indole-6-carboxylic acid

Product 1

HCID 39710543(1H-Indol-6-yl)(morpholino)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Hydroxy-7-azabenzotriazole (0.844 g, 6.21 mmol, 0.05 eq), EDCxHCl (26.09 g, 136.64 mmol, 1.1 eq) and morpholine (12.9 g, 149.06 mmol, 1.2 eq) were added to a stirred solution of 1H-indole-6-carboxylic acid (20.0 g, 124.22 mmol, 1.0 eq) in DMF (150 mL). Stirring was continued for 16 h at room temperature and water (200 mL) was then poured into the reaction mixture. The mixture was extracted with dichloromethane (2×150 mL) and the combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulphate and evaporated. White solid. Yield: 16.0 g (56% of theory).

Workup

  1. extractionThe mixture was extracted with dichloromethane (2×150 mL)
  2. washthe combined organic layers were washed with brine (100 mL)
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-46116f78130c414eae5361251f33a2f2
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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