Dimethylformamide → HCID 19891963, compound

HRID 893276Notes

Reaction equation

HRID 893276 reaction equation
[CH3:1]N(C=O)C.[H-].[Na+].[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([O:19][CH2:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][N:22]2[CH3:27])=[O:18])=[CH:9]1.CI>C1COCC1>[CH3:1][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([O:19][CH2:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][N:22]2[CH3:27])=[O:18])=[CH:9]1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19891949(1-Methyl-2-piperidinyl)methyl 1H-indole-3-carboxylate

Product 1

HCID 19891963HCID 19891963, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a DMF (10 ml) suspension of 60% sodium hydride (0.09 g, 2.3 mmol) was dropwise added a DMF (5 ml) solution of (1-methyl-2-piperidyl)methyl 1H-indole-3-carboxylate (0.50 g, 1.8 mmol) at room temperature over a period of 5 min. Onto the reaction mixture stirred for 15 min. was poured a THF (5 ml) solution of methyl iodide (0.29 g, 2.0 mmol). After stirring overnight, a reaction solution was poured onto water followed by extraction with EtOAc. The organic layer was washed successively with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product thus produced was purified by column chromatography on silica gel (20 g, CHCl3) to give 0.43 g of the title compound as a colorless oil.

Workup

  1. stirringAfter stirring overnight
  2. additiona reaction solution was poured onto water
  3. extractionfollowed by extraction with EtOAc
  4. washThe organic layer was washed successively with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product thus produced
  8. customwas purified by column chromatography on silica gel (20 g, CHCl3)

Sources & evidence

ORD record
ord-6595af5a7b85409e96adf005835ca59f
Source dataset
uspto-grants-1992_06
Patent number
US05124324

Reaction notes

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