Sodium hydride → HCID 23444808, compound

HRID 1840944Notes

Reaction equation

HRID 1840944 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][O:18][C:19]3[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=3[C:21]([O:23][CH3:24])=[O:22])[CH2:12][CH2:11]2)=[CH:2]1.[H-].[Na+].[CH2:31]([O:33][CH2:34][CH2:35]Br)[CH3:32]>CN(C=O)C>[CH2:31]([O:33][CH2:34][CH2:35][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][O:18][C:19]3[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=3[C:21]([O:23][CH3:24])=[O:22])[CH2:12][CH2:11]2)=[CH:2]1)[CH3:32]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 611412-Bromoethyl ethyl etherHCID 11440344methyl 2-{2-[4-(1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-benzoate

Product 1

HCID 23444808HCID 23444808, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.0 g (0.021 mol) of methyl 2-{2-[4-(1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-benzoate were dissolved in 125 ml of DMF and, at room temperature, 1.12 g (0.028 mol) of 60% sodium hydride was carefully added. This mixture was stirred for half an hour. 2.9 ml (0.023 mol) of 2-bromoethyl ethyl ether were dropwise added and the stirring was continued for 4 h. The solvent was evaporated under reduced pressure and the residue was worked-up as usual. The crude mixture was purified by flash-chromatography over silica gel affording 4.12 g (54% of yield) of methyl 2-(2-{4-[1-(2-ethoxy-ethyl)-1H-indol-3-yl]-piperidin-1-yl}-ethoxy)-benzoate

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe crude mixture was purified by flash-chromatography over silica gel affording 4.12 g (54% of yield) of methyl 2-(2-{4-[1-(2-ethoxy-ethyl)-1H-indol-3-yl]-piperidin-1-yl}-ethoxy)-benzoate

Sources & evidence

ORD record
ord-15a1aaa3ef154d85bdf16429672bf7a1
Source dataset
uspto-grants-2004_01
Patent number
US06683096B2

Reaction notes

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